FMOC-L-Leucine

Iupac Name：(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoic acid

Molecular Weight：353.418

Modify Date.: 2023-02-18 05:09

Introduction:

General procedure: To a solution of H-Phe-OH (100 mg, 60.5 mmol) in 50 percent MeCN (6.1 mL)were added Fmoc-OPhth (233 mg, 60.5 mmol) and K2CO3 (167 mg, 121 mmol) and stirred at room temperature. After 2 h of stirring saturated sodium bicarbonate solution and H2O were added and the resulting solution was washed with diethyl ether. The aqueous phase is acidified to pH 1 with 1M HCl and extracted with diethyl ether. The organic phase was washed with 1 M HCl, H2O, brine, dried over MgSO4. The filtrate was evaporatedevaporated under reduced pressure to give yellow solid as crude product.EXAMPLE 22

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1. Names and Identifiers

1.1 Name: FMOC-L-Leucine
1.2 Synonyms: (2R)-2-{[(9H-Fluoren-9-ylmethoxy)carbonyl]amino}-4-methylpentanoate (2S)-2-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)-4-methylpentanoic acid (2S)-2-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-4-methylpentanoic acid (2S)-2-[[[(9H-Fluoren-9-yl)methoxy]carbonyl]amino]-4-methylpentanoic acid 217: PN: US20070042401 PAGE: 29 claimed protein 908: PN: WO2006135786 PAGE: 58 claimed protein D-Leucine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, ion(1-) F-L-LEU Fmoc-leucine FMOC-LEU-OH FMOC-L-LEU FMOC-L-LEU-OH L-Leucine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]- L-Leucine-1-13C-N-FMOC N-(9-Fluorenylmethoxycarbonyl)leucine N-(9-Fluorenylmethoxycarbonyl)-L-leucine N-(Fluorenylmethoxycarbonyl)leucine N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-leucine N-FMOC-leucine N-Fmoc-L-leucine NPC 15199 NSC 334290

1.3 CAS No.: 35661-60-0

1.4 CID: 1549133

1.5 EINECS(EC#): 252-662-7

1.6 Molecular Formula: C21H23NO4 (isomer)

1.7 Inchi: InChI=1S/C21H23NO4/c1-13(2)11-19(20(23)24)22-21(25)26-12-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h3-10,13,18-19H,11-12H2,1-2H3,(H,22,25)(H,23,24)/t19-/m0/s1

1.8 InChkey: CBPJQFCAFFNICX-IBGZPJMESA-N

1.9 Canonical Smiles: CC(C)CC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

1.10 Isomers Smiles: CC(C)C[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

2. Properties

2.1 Density: 1.207

2.1 Melting point: 153-157℃

2.1 Boiling point: 559.8 °C at 760 mmHg

2.1 Refractive index: -25 ° (C=1, DMF)

2.1 Flash Point: 292.4 °C

2.1 Precise Quality: 353.16300

2.1 PSA: 75.63000

2.1 logP: 4.41530

2.1 Appearance: White crystalline powder

2.2 Storage: Keep Cold.

2.3 Chemical Properties: white to light yellow crystal powde

2.4 pKa: 3.91±0.21(Predicted)

2.5 Water Solubility: Appearance:White crystalline powder
Transport Information: OTH
Hazard Symbols:Not regulated UN NO.
particular:particular

2.6 Stability: Stable under normal temperatures and pressures.

2.7 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 7 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 5 of 7 companies. For more detailed information, please visit ECHA C&L website

Of the 1 notification(s) provided by 2 of 7 companies with hazard statement code(s):

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S24/25

4.1 Hazard Declaration: H302

4.1 RIDADR: OTH

4.1 Caution Statement: P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501

4.1 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

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : KBr disc

IR : nujol mull

Mass

7. Synthesis Route

35661-60-0Total: 14 Synthesis Route

61-90-5 649 Suppliers

35661-60-0 266 Suppliers

Literatures:
Chinchilla, Rafael; Dodsworth, David; Najera, Carmen; Soriano, Jose Tetrahedron Letters, 2001 , vol. 42, # 43 p. 7579 - 7581
Yield: ~71%

28920-43-6 225 Suppliers

35661-60-0 266 Suppliers

Literatures:
Helvetica Chimica Acta, , vol. 75, # 8 p. 2572 - 2582
Yield: null

146549-16-8

35661-60-0 266 Suppliers

Literatures:
Oppolzer, Wolfgang; Lienard, Philippe Helvetica Chimica Acta, 1992 , vol. 75, # 8 p. 2572 - 2582
Yield: ~93%

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8. Precursor and Product

precursor:

28920-43-6

61-90-5

168958-29-0

88744-04-1

102774-86-7

103321-59-1

82911-69-1

1227363-07-6

760-84-9

1131148-55-4

146549-16-8

127556-09-6

product :

86060-88-0

143744-88-1

58970-76-6

103321-59-1

193887-44-4

76542-83-1

103478-62-2

178933-95-4

71989-25-8

38689-31-5

58822-25-6

28540-82-1

38689-30-4

121377-67-1

133943-59-6

70774-25-3

157606-25-2

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9. Other Information

9.0 Mesh Entry Terms: N-(fluorenyl-9-methoxycarbonyl)leucine

10. Computational chemical data

Molecular Weight: 353.418g/mol
Molecular Formula: C₂₁H₂₃NO₄
Compound Is Canonicalized: True
XLogP3-AA: 4.4
Exact Mass: 353.16270821
Monoisotopic Mass: 353.16270821
Complexity: 484
Rotatable Bond Count: 7
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 75.6
Heavy Atom Count: 26
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: AAADceB6OAAAAAAAAAAAAAAAAAAAAYAAAAAwYAAAAAAAAGABQAAAHgAQCAAADSjhmAYyCILABgCIAiDSGAACAAAgAAAIiIGIAIkKIDKAkTCMYAAk1gEYiAeIwPAOgAAAAAAQAAAAAAAAACAAAQAACAAAAA==

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