(S)-Benzyl (1-amino-3-methyl-1-oxobutan-2-yl)carbamate

Base Information

• Chemical Name: (S)-Benzyl (1-amino-3-methyl-1-oxobutan-2-yl)carbamate
• CAS No.: 13139-28-1
• Molecular Formula: C13H18 N2 O3
• Molecular Weight: 250.298
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID90441807
• Nikkaji Number: J1.369.469I
• Wikidata: Q82258757
• Mol file: 13139-28-1.mol

Synonyms:13139-28-1;Z-Val-NH2;Z-L-valine amide;(S)-Benzyl (1-amino-3-methyl-1-oxobutan-2-yl)carbamate;benzyl N-[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]carbamate;N-Cbz-L-valinamide;MFCD00191170;SCHEMBL7305552;DTXSID90441807;AKOS016008560;NS-00012;CS-0155175;D70451;J-300301;benzyl N-[(1S)-1-carbamoyl-2-methylpropyl]carbamate;(S)-benzyl 1-amino-3-methyl-1-oxobutan-2-ylcarbamate;Carbamic acid, N-[(1S)-1-(aminocarbonyl)-2-methylpropyl]-, phenylmethyl ester

Chemical Property of (S)-Benzyl (1-amino-3-methyl-1-oxobutan-2-yl)carbamate

Chemical Property:

• PSA: 81.42000
• LogP: 2.51390
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 250.13174244
• Heavy Atom Count: 18
• Complexity: 286

Purity/Quality:

98%,99%, ^*data from raw suppliers

Z-L-valine amide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)N)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)[C@@H](C(=O)N)NC(=O)OCC1=CC=CC=C1

Technology Process of (S)-Benzyl (1-amino-3-methyl-1-oxobutan-2-yl)carbamate

There total 14 articles about (S)-Benzyl (1-amino-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: 98.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) → (S)-N-benzyloxycarbonylvalinamide (13139-28-1)

Guidance literature:

(S)-N-(benzyloxycarbonyl)valine; With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

With ammonium chloride; In N,N-dimethyl-formamide; at 23 ℃; for 16h;

Reference yield: 50.0%

Z-Leu-OH (2018-66-8) → (S)-N-benzyloxycarbonylvalinamide (13139-28-1)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; acetonitrile; for 0.5h; Ambient temperature; pH 3;

DOI:10.1021/ja00094a008

Reference yield: 25.0%

2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate (3496-11-5) → (S)-N-benzyloxycarbonylvalinamide (13139-28-1)

Guidance literature:

With ammonia; In chloroform; at 0 - 20 ℃; for 1.25h;

DOI:10.1021/jm980617f

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate

L-valine methylester hydrochloride

benzyl chloroformate

Downstream raw materials:

L-valinamide

[1-(1-Benzotriazol-1-yl-3-methyl-butylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester

(Z)-Z-Val-ΔPhe

Z-Val-ΔAla

Refernces

• 1、 Lalithamba,Uma,Gowthami,Nagendra. "Synthesis of Terminal Thiazoles from N-Protected Amino Acids and a Study of Their Antibacterial Activities". . p. 181 - 191. Retrieved 2020/03/30.
• 2、 -. "FUMAGILLOL COMPOUNDS AND METHODS OF MAKING AND USING SAME". Paragraph 00158. . Retrieved 2018/03/06.