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Home> Encyclopedia >   /  Enzymes  /  Pharmaceutical Intermediates  /  Organic Intermediate
N-(tert-Butoxycarbonyl)-L-glutamine structure
N-(tert-Butoxycarbonyl)-L-glutamine structure

N-(tert-Butoxycarbonyl)-L-glutamine

Iupac Name:(2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid
CAS No.: 13726-85-7
Molecular Weight:246.26032
Modify Date.: 2022-11-22 19:49
Introduction: Protected Glutamine. N-(tert-Butoxycarbonyl)-L-glutamineSupplier View more+
1. Names and Identifiers
1.1 Name
N-(tert-Butoxycarbonyl)-L-glutamine
1.2 Synonyms

(2S)-5-Amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid (S)-2-[(tert-Butoxycarbonyl)amino]-4-carbamoylbutanoic acid (S)-5-Amino-2-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid (S)-5-AMINO-2-(TERT-BUTOXYCARBONYLAMINO)-5-OXOPENTANOIC ACID (S)-5-Amino-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoic acid 5-Amino-2-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)-5-oxopentanoic acid Boc-D-Gln-OH BOC-GLN Boc-Gln-OH BOC-glutamine BOC-Glycine BOC-L-GLN BOC-L-GLN-OH BOC-L-glutamine BOC-L-GLUTAMINE extrapure Boc-L-glutamine, Nα-(tert-Butoxycarbonyl)-L-glutamine EINECS 237-296-8 Glutamine, N-[(1,1-dimethylethoxy)carbonyl]- Glutamine, N2-carboxy-, N2-tert-butyl ester, L- Glutamine, N2-carboxy-, N2-tert-butylester, L- (8CI) Glutamine, N2-carboxy-, N-tert-butyl ester Glutamine,N2-carboxy-, N-tert-butyl ester (7CI) L-Glutamine, N(2)-[(1,1-dimethylethoxy)carbonyl]- L-Glutamine, N-[(1,1-dimethylethoxy)carbonyl]- L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]- L-GLUTAMINE-N-T-BOC MFCD00065571 N-(tert-Butoxycarbonyl)glutamin N-(tert-Butoxycarbonyl)glutamine N-(tert-Butoxycarbonyl)-L-glutamin N-{[(2-Methyl-2-propanyl)oxy]carbonyl}glutamine N-{[(2-Methyl-2-propanyl)oxy]carbonyl}-L-glutamine N2-(tert-Butoxycarbonyl)-L-glutamine n2-[(1,1-dimethylethoxy)carbonyl]-l-glutamin N2-[(1,1-Dimethylethoxy)carbonyl]-L-glutamine N2-tert-Butoxycarbonyl-L-glutamine Na-(tert-Butoxycarbonyl)glutamine Na-(tert-Butoxycarbonyl)-L-glutamine N-Boc-glutamine N-Boc-L-glutamine NSC 334370 NSC334370 N-T-BOC-L-GLUTAMINE Nα-(tert-Butoxycarbonyl)glutamine Nα-(tert-Butoxycarbonyl)-L-glutamine Nα-Boc-L-glutamine Nα-tert-Butoxycarbonyl-L-glutamine TBOC-L-GLUTAMINE tert-Butoxycarbonyl-L-glutamine tert-butyloxycarbonyl-L-glutamine

1.3 CAS No.
13726-85-7
1.4 CID
83687
1.5 EINECS(EC#)
237-296-8
1.6 Molecular Formula
C10H18N2O5 (isomer)
1.7 Inchi
InChI=1S/C10H18N2O5/c1-10(2,3)17-9(16)12-6(8(14)15)4-5-7(11)13/h6H,4-5H2,1-3H3,(H2,11,13)(H,12,16)(H,14,15)/t6-/m0/s1
1.8 InChkey
VVNYDCGZZSTUBC-LURJTMIESA-N
1.9 Canonical Smiles
CC(C)(C)OC(=O)NC(CCC(=O)N)C(=O)O
1.10 Isomers Smiles
CC(C)(C)OC(=O)N[C@@H](CCC(=O)N)C(=O)O
2. Properties
3.1 Density
1.22
3.1 Melting point
114-117℃
3.1 Boiling point
509.1°Cat760mmHg
3.1 Refractive index
-4 ° (C=2, EtOH)
3.1 Flash Point
261.7°C
3.1 Precise Quality
246.12200
3.1 PSA
118.72000
3.1 logP
1.32100
3.1 Solubility
Soluble in DMSO and methanol. Soluble in 1 mmole in 2 ml DMF.
3.2 Appearance
White powder.
3.3 Storage
Keep Cold.
3.4 Chemical Properties
White fine crystalline powder
3.5 pKa
3.84±0.10(Predicted)
3.6 Water Solubility
Soluble in DMSO and methanol. Soluble in 1 mmole in 2 ml DMF.
3.7 Stability
Stable under normal temperatures and pressures.
3.8 StorageTemp
Sealed in dry,2-8°C
3. Use and Manufacturing
4.1 Methods of Manufacturing
N (Boc)-L-Glutamine (1): L-Glutamine (25g, 0.l7lmol) (Procured fromSpectrochem chemicals) was dissolved in (300 mL) of aqueous solution of NaOH (21.9, 0.547 mol).The solution was cooled and a solution of Boc anhydride (0.205) in THF (150 mL) was added at <10°C (Exothermic reaction).Then the reaction mixture was stirred at 25°C for 20 h. TLC control: MeOH, CH2C12 (1:1) with 0.1percent AcOH. The organic phase was separated off, the water phase was extracted with hexane (100 mL), and acidified by 2N HCLto pH 2, and extracted with ethyl acetate (2x250 mE). Combined organic phase was dried over Na2SO4, then evaporated by vacuum, diluted with methylene chloride, and evaporated again. The product is obtained as a sticky oil, which could be crystallized by hexanc to after standing for 2-3 days to yield N-(Boc)-L-glutamine (1) (37.5g, 89percent)as colorless solid.1H NMR (DMSO, 300 MHz) 7.27 (111, s, OH), 6.97 (2H, d, J=7.92Hz, NH), 3.83 (1H, m, J=4.29 Hz, H-3), 2.09 (211, t, J=9.54 Hz, H-5), 1.9082-1.6856 (2H, m, H-4), 1.3687 (9H, s, H-6) ESI-MS (m/z):269(M+Na)Glutamine 2KG, 10percent sodium carbonate solution 40 liters, stirred to dissolve, add acetone 20 liters, and then at room temperature was added dropwise a mixture of di-tert-butyl dicarbonate 5KG and 4 liters of acetone, while constantly adjusted with sodium carbonate PH = 8 -9, at room temperature overnight.The mixture was adjusted to pH 2 with 3N hydrochloric acid and extracted five times with ethyl acetate. The combined ethyl acetate was washed three times with saturated brine and the ethyl acetate was distilled off to obtain 1.3 kg of tert-butoxycarbonyl-L-glutamine.
4.2 Usage
Protected Glutamine. N-(tert-Butoxycarbonyl)-L-glutamineSupplier
4. Safety and Handling
5.1 Risk Statements
S22-S24/25
5.1 Safety Statements
S24/25
5.1 RIDADR
NONH for all modes of transport
5.1 WGK Germany
3
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 BRN
2127805
9.1 Chemical Properties
White fine crystalline powder
9.2 Uses
Protected Glutamine.
9.3 Usage
It is employed in the synthesis and analgesic activity of human .beta.-endorphin.
9.4 Storage Conditions
N (Boc)-L-Glutamine (1): L-Glutamine (25g, 0.l7lmol) (Procured fromSpectrochem chemicals) was dissolved in (300 mL) of aqueous solution of NaOH (21.9, 0.547 mol).The solution was cooled and a solution of Boc anhydride (0.205) in THF (150 mL) was added at <10°C (Exothermic reaction).Then the reaction mixture was stirred at 25°C for 20 h. TLC control: MeOH, CH2C12 (1:1) with 0.1percent AcOH. The organic phase was separated off, the water phase was extracted with hexane (100 mL), and acidified by 2N HCLto pH 2, and extracted with ethyl acetate (2x250 mE). Combined organic phase was dried over Na2SO4, then evaporated by vacuum, diluted with methylene chloride, and evaporated again. The product is obtained as a sticky oil, which could be crystallized by hexanc to after standing for 2-3 days to yield N-(Boc)-L-glutamine (1) (37.5g, 89percent)as colorless solid.1H NMR (DMSO, 300 MHz) 7.27 (111, s, OH), 6.97 (2H, d, J=7.92Hz, NH), 3.83 (1H, m, J=4.29 Hz, H-3), 2.09 (211, t, J=9.54 Hz, H-5), 1.9082-1.6856 (2H, m, H-4), 1.3687 (9H, s, H-6) ESI-MS (m/z):269(M+Na)Glutamine 2KG, 10percent sodium carbonate solution 40 liters, stirred to dissolve, add acetone 20 liters, and then at room temperature was added dropwise a mixture of di-tert-butyl dicarbonate 5KG and 4 liters of acetone, while constantly adjusted with sodium carbonate PH = 8 -9, at room temperature overnight.The mixture was adjusted to pH 2 with 3N hydrochloric acid and extracted five times with ethyl acetate. The combined ethyl acetate was washed three times with saturated brine and the ethyl acetate was distilled off to obtain 1.3 kg of tert-butoxycarbonyl-L-glutamine.
9.5 Manufacturing Info
L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]-: INACTIVE
10. Computational chemical data
  • Molecular Weight: 246.26032g/mol
  • Molecular Formula: C10H18N2O5
  • Compound Is Canonicalized: True
  • XLogP3-AA: -0.2
  • Exact Mass: 246.12157168
  • Monoisotopic Mass: 246.12157168
  • Complexity: 308
  • Rotatable Bond Count: 7
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Topological Polar Surface Area: 119
  • Heavy Atom Count: 17
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceBzOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQCAAADGzBgAQCCALABgAIAAGQGAAAAAAAAAAAAIGIAAECABIAgCAMQAAEFgAQAACcFwAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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