(2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-phenylbutanoic acid

Base Information

• Chemical Name: (2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-phenylbutanoic acid
• CAS No.: 90731-57-0
• Molecular Formula: C15H20NO4-
• Molecular Weight: 279.336
• Hs Code.: 29225000
• Nikkaji Number: J1.068.365C
• Mol file: 90731-57-0.mol

Synonyms:90731-57-0;115132-19-9;(2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-phenylbutanoic acid;N-BOC-ERYTHRO-L-BETA-METHYLPHENYLALANINE;(2S,3S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylbutanoic acid;(2S,3S)-N-Boc-2-Amino-3-phenylbutyric acid;(2r, 3r)/(2s, 3s)-racemic-boc-beta-methyl-phenylalanine;(2R,3R)/(2S,3S)-racemic-Boc-beta-methyl-phenylalanine;(2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-phenylbutanoic acid;N-Boc-erythro-L-b-methylphenylalanine;(2s, 3s)-boc-beta-methyl-phenylalanine;(2S,3S)-2-Boc-amino-3-phenyl-butyric acid;SCHEMBL844407;Boc-(2S,3S)--MePhe-OH;XFSLNPBJZAPTMM-JQWIXIFHSA-N;AMY19208;MFCD00800584;MFCD01456490;(2S,3S)-Boc-beta-methyl-L-Phe-OH;AKOS022186565;AT10040;(2S,3S)-Boc-beta-methyl-phenylalanine;CS-0136335;A843626;N-Boc-erythro-L-beta-methylphenylalanine, AldrichCPR;(S, S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid;(S,S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid;(2S, 3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid;(2S,3S)-2-(tert-butoxycarbonylamino)-3-phenyl-butanoate;(2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid;(2S,3S)-2-(tert-butoxycarbonylamino)-3-phenylbutanoic acid;(2S,3S)-2-[(tert-Butyloxycarbonyl)amino]-3-phenylbutyric acid;N-Boc-erythro-DL-beta-methylphenylalanine (Boc-L-Phe(bS-Me)-OH)

Chemical Property of (2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-phenylbutanoic acid

Chemical Property:

• Vapor Pressure: 4.79E-08mmHg at 25°C
• Melting Point: 100-105 °C
• Boiling Point: 426.8°C at 760 mmHg
• PKA: 3.90±0.10(Predicted)
• Flash Point: 211.9°C
• PSA: 81.95000
• Density: 1.135±0.06 g/cm3(Predicted)
• LogP: 1.63770
• Storage Temp.: 0-6°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 279.14705815
• Heavy Atom Count: 20
• Complexity: 342

Purity/Quality:

98%min ^*data from raw suppliers

N-Boc-erythro-L-beta-methylphenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-phenylbutanoic acid

There total 16 articles about (2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-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: 77.0%

(2S,3S)-2-<(tert-butoxycarbonyl)amino>-3-phenylbutanol (218797-68-3) → (βS)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine (90731-57-0,630424-76-9)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; for 24h;

DOI:10.1021/jo981140i

Reference yield:

(S)-3-Phenyl-2-(2,2,2-trifluoro-acetylamino)-butyric acid (117918-24-8) → (βS)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine (90731-57-0,630424-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / H₂O / 48 h / 39 °C / biosynthesis by carboxypeptidase, pH 7.2

2: triethylamine / H₂O; butan-1-ol

With triethylamine; In water; butan-1-ol;

DOI:10.1021/jm00122a030

Reference yield:

(S)-2-Amino-3-phenyl-butyric acid (25488-24-8,134235-83-9) → (βS)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine (90731-57-0,630424-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / 1 h / ice-cooling

2: 74 percent / H₂O / 48 h / 39 °C / biosynthesis by carboxypeptidase, pH 7.2

3: triethylamine / H₂O; butan-1-ol

With triethylamine; In water; trifluoroacetic acid; butan-1-ol;

DOI:10.1021/jm00122a030

upstream raw materials:

tert-butyldicarbonate

(2S,3S)-methylphenylalanine

(2S,3S)-2-<(tert-butoxycarbonyl)amino>-3-phenylbutanol

(2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol

Downstream raw materials:

(2S,3S)-2-amino-1-(1,2-oxazinan-2-yl)-3-phenylbutan-1-one, trifluoroacetic acid salt

(3S,4S)-3-amino-1-(benzyloxy)-4-methyl-3,4-dihydroquinolin-2(1H)-one

Refernces

• 1、 Zhou, Changyou,Garcia-Calvo, Margareta,Pinto, Shirly,Lombardo, Matthew,Feng, Zhe,Bender, Kate,Pryor, Kellyann D.,Bhatt, Urmi R.,Chabin, Renee M.,Geissler, Wayne M.,Shen, Zhu,Tong, Xinchun,Zhang, Zhoupeng,Wong, Kenny K.,Roy, Ranabir Sinha,Chapman, Kevin T.,Yang, Lihu,Xiong, Yusheng. "Design and synthesis of prolylcarboxypeptidase (PrCP) inhibitors to validate PrCP as a potential target for obesity". experimental part. p. 7251 - 7263. Retrieved 2010/12/25.
• 2、 Samanen, J.,Narindray, D.,Cash, T.,Brandeis, E.,Adams, W.,et al.. "Potent Angiotensin II Antagonists with Non-β-branched Aminoacids in Position 5". . p. 466 - 472. Retrieved 2007/10/02.