(S)-(9H-Fluoren-9-yl)methyl (1-chloro-3-methyl-1-oxobutan-2-yl)carbamate

Base Information

• Chemical Name: (S)-(9H-Fluoren-9-yl)methyl (1-chloro-3-methyl-1-oxobutan-2-yl)carbamate
• CAS No.: 103321-53-5
• Molecular Formula: C20H20 Cl N O3
• Molecular Weight: 357.837
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID10448232
• Nikkaji Number: J362.277K
• Wikidata: Q82267206
• Mol file: 103321-53-5.mol

Synonyms:Fmoc-Val-Cl;103321-53-5;Fmoc-L-Valinyl chloride;(S)-(9H-Fluoren-9-yl)methyl (1-chloro-3-methyl-1-oxobutan-2-yl)carbamate;9H-FLUOREN-9-YLMETHYL N-[(2S)-1-CHLORO-3-METHYL-1-OXOBUTAN-2-YL]CARBAMATE;(S)-(9H-fluoren-9-yl)methyl 1-chloro-3-methyl-1-oxobutan-2-ylcarbamate;Fmoc-L-Val-Chloride;SCHEMBL6779154;DTXSID10448232;OJVUGYYHLWTNDI-SFHVURJKSA-N;MFCD00235840;AS-75539;A896506;J-000933

Chemical Property of (S)-(9H-Fluoren-9-yl)methyl (1-chloro-3-methyl-1-oxobutan-2-yl)carbamate

Chemical Property:

• Melting Point: 110-111 °C
• Boiling Point: 508.7±33.0 °C(Predicted)
• PKA: 10.27±0.46(Predicted)
• PSA: 55.40000
• Density: 1.233±0.06 g/cm3(Predicted)
• LogP: 4.70600
• Storage Temp.: Store at 0°C
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 357.1131712
• Heavy Atom Count: 25
• Complexity: 473

Purity/Quality:

98.5% ^*data from raw suppliers

Fmoc-Val-Cl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)Cl)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)[C@@H](C(=O)Cl)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of (S)-(9H-Fluoren-9-yl)methyl (1-chloro-3-methyl-1-oxobutan-2-yl)carbamate

There total 1 articles about (S)-(9H-Fluoren-9-yl)methyl (1-chloro-3-methyl-1-oxobutan-2-yl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Fmoc-Val-OH (68858-20-8) → (S)-(9H-fluoren-9-yl)methyl 1-chloro-3-methyl-1-oxobutan-2-ylcarbamate (103321-53-5)

Guidance literature:

With thionyl chloride; In dichloromethane; at 55 - 60 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.200800359

Reference yield: 96.0%

(S)-(9H-fluoren-9-yl)methyl 1-chloro-3-methyl-1-oxobutan-2-ylcarbamate (103321-53-5) + 2-chloro-5-nitrobenzaldehyde (6361-21-3) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-thiobutyric acid S-(2-formyl-4-nitro-phenyl) ester (557095-50-8)

Guidance literature:

2-chloro-5-nitrobenzaldehyde; With sodium sulfide; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 12h;

(S)-(9H-fluoren-9-yl)methyl 1-chloro-3-methyl-1-oxobutan-2-ylcarbamate; In tetrahydrofuran; N,N-dimethyl-formamide; at -78 - -50 ℃; for 3h;

DOI:10.1016/S0040-4039(03)00471-4

Reference yield: 91.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + (S)-(9H-fluoren-9-yl)methyl 1-chloro-3-methyl-1-oxobutan-2-ylcarbamate (103321-53-5) → Fmoc-Val-OPfp (86060-87-9)

Guidance literature:

With pyridine; In tetrahydrofuran; at 4 ℃;

DOI:10.1016/0040-4039(91)80788-8

upstream raw materials:

Fmoc-Val-OH

Downstream raw materials:

Fmoc-Val-OPfp

N-<(9-fluorenylmethyl)oxy>carbonylvalyl-N-methylleucylalanine benzyl ester

{(S)-1-[3-(2-Benzyloxycarbonylamino-acetyl)-3,4-dihydro-1H-phthalazine-2-carbonyl]-2-methyl-propyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

N-α-(9-fluorenylmethyloxycarbonyl)-L-valinal

Refernces

• 1、 Duttagupta, Indranil,Misra, Debojyoti,Bhunya, Sourav,Paul, Ankan,Sinha, Surajit. "Cis-Trans Conformational Analysis of δ-Azaproline in Peptides". . p. 10585 - 10604. Retrieved 2015.
• 2、 Duttagupta, Indranil,Bhadra, Jhuma,Das, Sanjib Kr.,Sinha, Surajit. "Proteolytic stability of cyclic α-hydrazino acid containing peptides: a qualitative study". . p. 3858 - 3861. Retrieved 2016.
• 3、 Cavelier,Gomez,Jacquier,Llinares,Mercadier,Petrus,Verducci. "Determination of the enantiomeric excess of α-hydroxy acids". . p. 2495 - 2500. Retrieved 1993.
• 4、 Kantharaju, Kamanna,Khatavi, Santosh Y.. "Eco-friendly synthesis of peptides using fmoc-amino acid chlorides as coupling agent under biphasic condition". . p. 699 - 707. Retrieved 2021/08/23.
• 5、 -. "Amide prodrug derivatives as protein kinase inhibitors". Paragraph 0126; 0161-0164. . Retrieved 2019/02/04.