(S)-3-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid

Base Information

• Chemical Name: (S)-3-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid
• CAS No.: 26250-86-2
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.353
• DSSTox Substance ID: DTXSID301190409
• Nikkaji Number: J1.374.270G
• Mol file: 26250-86-2.mol

Synonyms:26250-86-2;(S)-3-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid;Benzenebutanoic acid, b-[[(phenylmethoxy)carbonyl]amino]-, (bS)-;(3S)-3-{[(Benzyloxy)carbonyl]amino}-4-phenylbutanoic acid;SCHEMBL6157326;DTXSID301190409;MFCD31591418;AKOS037649032;BS-16331;CS-0162046;D80662;EN300-816819;(3S)-3-(Benzyloxycarbonylamino)-4-phenylbutyric acid;(3S)-4-phenyl-3-(phenylmethoxycarbonylamino)butanoic acid;(S)-3-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoicacid;(betaS)-beta-[[(Phenylmethoxy)carbonyl]amino]benzenebutanoic acid

Chemical Property of (S)-3-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid

Chemical Property:

• Melting Point: 118-119 °C
• Boiling Point: 526.7±50.0 °C(Predicted)
• Density: 1.222±0.06 g/cm3(Predicted)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 313.13140809
• Heavy Atom Count: 23
• Complexity: 373

Purity/Quality:

99%, ^*data from raw suppliers

(S)-3-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(CC(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](CC(=O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of (S)-3-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid

There total 30 articles about (S)-3-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid 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: 97.0%

(S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone (15196-02-8) → (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid (26250-86-2)

Guidance literature:

With silver trifluoroacetate; silica gel; In ethyl acetate; at 50 ℃; for 0.25h;

DOI:10.1080/00397910500290466

Reference yield: 92.0%

(S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone (15196-02-8) + silver benzoate (532-31-0) → (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid (26250-86-2)

Guidance literature:

In 1,4-dioxane; water; for 6h; Reflux;

DOI:10.1016/j.tet.2014.05.098

Reference yield: 84.0%

allyl (S)-3-benzyloxycarbonylamino-4-phenylbutanoate (374783-65-0) → (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid (26250-86-2)

Guidance literature:

With lithium hydroxide; In methanol; for 17h;

DOI:10.1016/S0040-4020(01)00731-1

upstream raw materials:

methyl N-(benzyloxycarbonyl)-(3S)-3-amino-4-phenylbutanoate

(S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone

β-homo-(S)-phenylalanine

benzyl chloroformate

Downstream raw materials:

(S)-3-Benzyloxycarbonylamino-4-phenyl-butyric acid tert-butyl ester

(S)-3-(benzyloxycarbonylamino)-4-phenylbutyl methanesulfonate

(S)-3-amino-4-phenylbutane-1-sulfonic acid

(S)-3-benzyloxycarbonylamino-4-phenylbutane-1-sulfonic acid

Refernces

• 1、 Zheng, Yongpeng,Xu, Jiaxi. "Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids". . p. 5197 - 5206. Retrieved 2014/12/10.
• 2、 Sleebs, Brad E.,Nguyen, Nghi H.,Hughes, Andrew B.. "A mild multistep conversion of n-protected α-amino acids into N-protected β3-amino acids utilizing the Nef reaction". . p. 747 - 751. Retrieved 2013/05/08.