(R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester

Base Information

• Chemical Name: (R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester
• CAS No.: 139377-46-1
• Molecular Formula: C₃₅H₄₀BrN₃O₁₀
• Molecular Weight: 742.621

Synonyms:(R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester

Chemical Property of (R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester

Chemical Property:

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Technology Process of (R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester

There total 7 articles about (R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester 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:

3-(4-chlorophenyl)propanoic acid (2019-34-3) → (R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester (139377-46-1)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N / tetrahydrofuran / a) -78 deg C, 10 min, b) 0 deg C, 30 min

2: 1) n-BuLi / 1) hexane, THF, -78 deg C, 2) a) -78 deg C, 15 min, b) up to room temp., 45 min

3: 1) KHMDS, 2) trisyl azide / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 2 min

4: aq. LiOH, 30percent H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

5: 1) Et₃N, HOBt, 2) DCC / 1) DMF, 0 deg C, 2) a) 2 h, 0 deg C, b) 17 h, room temp.

6: H₂ / 10percent Pd/C / ethyl acetate / 1.5 h / Ambient temperature

With lithium hydroxide; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate;

DOI:10.1021/jo00032a028

Reference yield:

C14H17ClO3 (1027659-22-8) → (R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester (139377-46-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) n-BuLi / 1) hexane, THF, -78 deg C, 2) a) -78 deg C, 15 min, b) up to room temp., 45 min

2: 1) KHMDS, 2) trisyl azide / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 2 min

3: aq. LiOH, 30percent H₂O₂ / tetrahydrofuran; H₂O / 1 h / 0 °C

4: 1) Et₃N, HOBt, 2) DCC / 1) DMF, 0 deg C, 2) a) 2 h, 0 deg C, b) 17 h, room temp.

5: H₂ / 10percent Pd/C / ethyl acetate / 1.5 h / Ambient temperature

With lithium hydroxide; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate;

DOI:10.1021/jo00032a028

Reference yield:

(R)-2-Azido-3-(4-chloro-phenyl)-propionic acid (139377-27-8) → (R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester (139377-46-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) Et₃N, HOBt, 2) DCC / 1) DMF, 0 deg C, 2) a) 2 h, 0 deg C, b) 17 h, room temp.

2: H₂ / 10percent Pd/C / ethyl acetate / 1.5 h / Ambient temperature

With hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethyl acetate;

DOI:10.1021/jo00032a028

upstream raw materials:

(R)-Benzyloxycarbonylamino-(3-hydroxy-phenyl)-acetic acid methyl ester

D-(+)-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanylglycine 2-bromoethyl ester

3-(4-chlorophenyl)propanoic acid

C₁₄H₁₇ClO₃

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