2-[(R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-oxo-butyric acid ethyl ester

Base Information

• Chemical Name: 2-[(R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-oxo-butyric acid ethyl ester
• CAS No.: 168470-53-9
• Molecular Formula: C₂₅H₂₇N₃O₆
• Molecular Weight: 465.506

Synonyms:2-[(R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-oxo-butyric acid ethyl ester

Chemical Property of 2-[(R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-oxo-butyric acid ethyl ester

Chemical Property:

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Technology Process of 2-[(R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-oxo-butyric acid ethyl ester

There total 2 articles about 2-[(R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-oxo-butyric acid 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:

N-(benzyloxycarbonyl)-D-tryptophan (2279-15-4) → 2-[(R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-oxo-butyric acid ethyl ester (168470-53-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N-methylmorpholine / tetrahydrofuran / 0.5 h / -20 °C

2: N-methylmorpholine / dimethylformamide; tetrahydrofuran / 1 h / Ambient temperature

With 4-methyl-morpholine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm950591h

Reference yield:

ethyl 2-amino-3-oxobutanoate hydrochloride (20207-16-3) + C24H26N2O6 (133641-28-8) → 2-[(R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-oxo-butyric acid ethyl ester (168470-53-9)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; N,N-dimethyl-formamide; for 1h; Yield given; Ambient temperature;

DOI:10.1021/jm950591h

Reference yield: 73.0%

2-[(R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-oxo-butyric acid ethyl ester (168470-53-9) → 2-[(R)-1-Benzyloxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-5-methyl-1H-imidazole-4-carboxylic acid ethyl ester (168470-54-0)

Guidance literature:

With ammonium acetate; acetic acid; for 16h; Heating;

DOI:10.1021/jm950591h

upstream raw materials:

ethyl 2-amino-3-oxobutanoate hydrochloride

C₂₄H₂₆N₂O₆

N-(benzyloxycarbonyl)-D-tryptophan

Downstream raw materials:

2-[(R)-1-Benzyloxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-5-methyl-thiazole-4-carboxylic acid ethyl ester

2-[(R)-1-Benzyloxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-5-methyl-1H-imidazole-4-carboxylic acid ethyl ester

2-[(R)-1-Benzyloxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-5-methyl-oxazole-4-carboxylic acid ethyl ester

2-[(R)-1-{(S)-2-[(Azepane-1-carbonyl)-amino]-4-methyl-pentanoylamino}-2-(1H-indol-3-yl)-ethyl]-5-methyl-thiazole-4-carboxylic acid ethyl ester

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