(S)-2-(BENZYLOXYCARBONYLAMINO)-2-PHENYLPROPANOIC ACID

Base Information

• Chemical Name: (S)-2-(BENZYLOXYCARBONYLAMINO)-2-PHENYLPROPANOIC ACID
• CAS No.: 169738-78-7
• Molecular Formula: C17H17NO4
• Molecular Weight: 299.32
• Mol file: 169738-78-7.mol

Synonyms:(S)-2-(BENZYLOXYCARBONYLAMINO)-2-PHENYLPROPANOIC ACID;(S)-CBZ-ALPHA-METHYL-PHENYLGLYCINE

Chemical Property of (S)-2-(BENZYLOXYCARBONYLAMINO)-2-PHENYLPROPANOIC ACID

Chemical Property:

• Boiling Point: 501.1±50.0 °C(Predicted)
• PKA: 3.54±0.10(Predicted)
• PSA: 75.63000
• Density: 1.245±0.06 g/cm3(Predicted)
• LogP: 3.30370

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(BENZYLOXYCARBONYLAMINO)-2-PHENYLPROPANOIC ACID

There total 4 articles about (S)-2-(BENZYLOXYCARBONYLAMINO)-2-PHENYLPROPANOIC 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: 95.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (S)-2-methyl-2-phenylglycine (13398-26-0,6945-32-0) → (S)-N2-<(benzyloxy)carbonyl>-2-methyl-2-phenylglycine (169738-78-7)

Guidance literature:

With sodium hydroxide; sodium hydrogencarbonate; In 1,4-dioxane; at 20 ℃; for 384h;

DOI:10.1016/j.tetasy.2004.04.044

Reference yield: 80.0%

(4S,5S)-4-[(S)-(1-N-(benzoyloxycarbonylamino-1-phenyl)ethyl)]-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane → (S)-N2-<(benzyloxy)carbonyl>-2-methyl-2-phenylglycine (169738-78-7)

Guidance literature:

(4S,5S)-4-[(S)-(1-N-(benzoyloxycarbonylamino-1-phenyl)ethyl)]-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane; With toluene-4-sulfonic acid; In methanol; at 60 ℃; for 12h;

With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 8h;

With potassium permanganate; sodium dihydrogenphosphate; In tert-butyl alcohol; at 20 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(98)00503-1

Reference yield:

(4S,5S)-4-[(S)-(1-amino-1-phenyl)ethyl]-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane → (S)-N2-<(benzyloxy)carbonyl>-2-methyl-2-phenylglycine (169738-78-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / Diisopropylethylamine / acetonitrile / 20 °C / TLC-monitoring

2.1: TsOH / methanol / 12 h / 60 °C

2.2: NaIO₄ / tetrahydrofuran; H₂O / 8 h / 20 °C

2.3: 80 percent / KMnO₄; NaH₂PO₄ / 2-methyl-propan-2-ol / 0.17 h / 20 °C

With toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In methanol; acetonitrile; 1.1: Acylation / 2.1: Ring cleavage / 2.2: Oxidation / 2.3: Oxidation;

DOI:10.1016/S0040-4020(98)00503-1

upstream raw materials:

(S)-2-methyl-2-phenylglycine

benzyl chloroformate

N-(Benzyloxycarbonyloxy)succinimide

Downstream raw materials:

C₃₄H₃₂N₂O₇

(S)-2-((S)-2-Benzyloxycarbonylamino-2-phenyl-propionylamino)-2-phenyl-propionic acid tert-butyl ester

(R)-2-((S)-2-Benzyloxycarbonylamino-2-phenyl-propionylamino)-2-phenyl-propionic acid tert-butyl ester

[(S)-1-((R)-1-Carbamoyl-1-phenyl-ethylcarbamoyl)-1-phenyl-ethyl]-carbamic acid benzyl ester

Refernces

• 1、 Mueller, Simona,Ariaans, Gerry J. A.,Kaptein, Bernard,Broxterman, Quirinus B.,Formaggio, Fernando,Battan, Elisa,Crisma, Marco,Toniolo, Claudio,Bruggink, Alle. "Exploring new dipeptides based on phenylglycine and Cα- methyl phenylglycine as hosts in inclusion resolutions". . p. 1919 - 1927. Retrieved 2007/10/03.
• 2、 Obrecht,Bohdal,Broger,Bur,Lehmann,Ruffieux,Schonholzer,Spiegler,Muller. "L-phenylalanine cyclohexylamide: A simple and convenient auxiliary for the synthesis of optically pure α,α-disubstituted (R)- and (S)-amino acids". . p. 563 - 580. Retrieved 2007/10/02.