(S)-2-(3-Benzyloxymethyl-3H-imidazol-4-ylmethyl)-3-hydroxy-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-(3-Benzyloxymethyl-3H-imidazol-4-ylmethyl)-3-hydroxy-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester
• CAS No.: 120742-08-7
• Molecular Formula: C₂₁H₂₅N₃O₅
• Molecular Weight: 399.447

Synonyms:(S)-2-(3-Benzyloxymethyl-3H-imidazol-4-ylmethyl)-3-hydroxy-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

Chemical Property of (S)-2-(3-Benzyloxymethyl-3H-imidazol-4-ylmethyl)-3-hydroxy-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of (S)-2-(3-Benzyloxymethyl-3H-imidazol-4-ylmethyl)-3-hydroxy-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

There total 2 articles about (S)-2-(3-Benzyloxymethyl-3H-imidazol-4-ylmethyl)-3-hydroxy-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl 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-[(1,1-dimethylethoxy)carbonyl]-3-[(phenylmethoxy)methyl]-L-histidine (79950-65-5,99310-01-7) → (S)-2-(3-Benzyloxymethyl-3H-imidazol-4-ylmethyl)-3-hydroxy-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (120742-08-7)

Guidance literature:

Multi-step reaction with 2 steps

1: DMAP, DCC / CH₂Cl₂ / 24 h / Ambient temperature

2: acetonitrile / 0.5 h / 110 deg C bath temperature

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile;

DOI:10.1021/jm00127a028

Reference yield:

5-<1-Hydroxy-2(S)-<(tert-butyloxycarbonyl)amino>-3-<3-(benzyloxymethyl)imidazol-4-yl>propylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione (120742-07-6) → (S)-2-(3-Benzyloxymethyl-3H-imidazol-4-ylmethyl)-3-hydroxy-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (120742-08-7)

Guidance literature:

In acetonitrile; for 0.5h; 110 deg C bath temperature;

DOI:10.1021/jm00127a028

Reference yield:

(S)-2-(3-Benzyloxymethyl-3H-imidazol-4-ylmethyl)-3-hydroxy-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (120742-08-7) → (4S,5S)-1-(tert-Butyloxycarbonyl)-4-hydroxy-5-<<3-(benzyloxymethyl)imidazol-4-yl>methyl>pyrrolidin-2-one (120742-09-8)

Guidance literature:

With sodium tetrahydroborate; acetic acid; In dichloromethane; at 0 ℃; for 4h; Yield given;

DOI:10.1021/jm00127a028

upstream raw materials:

5-<1-Hydroxy-2(S)-<(tert-butyloxycarbonyl)amino>-3-<3-(benzyloxymethyl)imidazol-4-yl>propylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione

N-[(1,1-dimethylethoxy)carbonyl]-3-[(phenylmethoxy)methyl]-L-histidine

Downstream raw materials:

(4S,5S)-1-(tert-Butyloxycarbonyl)-4-hydroxy-5-<<3-(benzyloxymethyl)imidazol-4-yl>methyl>pyrrolidin-2-one

(3S,4R)-5-(3-Benzyloxymethyl-3H-imidazol-4-yl)-3-hydroxy-4-{(S)-3-methyl-2-[(S)-3-methyl-2-(3-methyl-butyrylamino)-butyrylamino]-butyrylamino}-pentanoic acid methyl ester

N-Isovaleryl-L-Valyl-L-Valyl-4(S)-amino-5-<3-(benzyloxymethyl)imidazol-4-yl>-3(S)-hydroxypentanoic Acid Methyl Ester

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