2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 2-oxo-2-phenyl-ethyl ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 2-oxo-2-phenyl-ethyl ester
• CAS No.: 1067920-63-1
• Molecular Formula: C₂₄H₂₆N₂O₅
• Molecular Weight: 422.481

Synonyms:2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 2-oxo-2-phenyl-ethyl ester

Chemical Property of 2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 2-oxo-2-phenyl-ethyl ester

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Technology Process of 2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 2-oxo-2-phenyl-ethyl ester

There total 1 articles about 2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 2-oxo-2-phenyl-ethyl 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:

Boc-D-Trp-OH (5241-64-5) + α-bromoacetophenone (70-11-1) → 2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 2-oxo-2-phenyl-ethyl ester (1067920-63-1)

Guidance literature:

Boc-D-Trp-OH; With caesium carbonate; In N,N-dimethyl-formamide;

α-bromoacetophenone; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00107-X

Reference yield:

2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 2-oxo-2-phenyl-ethyl ester (1067920-63-1) → tert-butyl[(1R)-2-(1H-indol-3-yl)-1-(5-phenyl-1H-imidazol-2-yl)ethyl]carbamate (335243-50-0)

Guidance literature:

With ammonium acetate; In xylene; Heating;

DOI:10.1016/S0960-894X(01)00107-X

Reference yield:

2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 2-oxo-2-phenyl-ethyl ester (1067920-63-1) → C28H24N4

Guidance literature:

Multi-step reaction with 3 steps

1: NH₄OAc / xylene / 0.75 h / Heating

2: 99 percent / HCl(g) / ethyl acetate / 0 °C

3: 24 percent / butan-1-ol / Heating

With hydrogenchloride; ammonium acetate; In ethyl acetate; xylene; butan-1-ol; 3: Pictet-Spengler cyclization;

DOI:10.1021/jm0108449

upstream raw materials:

Boc-D-Trp-OH

α-bromoacetophenone

Downstream raw materials:

tert-butyl[(1R)-2-(1H-indol-3-yl)-1-(5-phenyl-1H-imidazol-2-yl)ethyl]carbamate

(1R)-2-(1H-indol-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)-1-ethanamine

(1S,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline

(1R,3R)-3-(4-phenyl-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carboline

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