(S)-2-{Methyl-[(R)-3-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-butyl]-carbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-2-{Methyl-[(R)-3-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-butyl]-carbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester
• CAS No.: 161708-51-6
• Molecular Formula: C₂₅H₃₈N₂O₅Si
• Molecular Weight: 474.673

Synonyms:(S)-2-{Methyl-[(R)-3-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-butyl]-carbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

Chemical Property of (S)-2-{Methyl-[(R)-3-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-butyl]-carbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (S)-2-{Methyl-[(R)-3-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-butyl]-carbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

There total 11 articles about (S)-2-{Methyl-[(R)-3-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-butyl]-carbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid benzyl 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:

2-(Trimethylsilyl)ethanol (2916-68-9) → (S)-2-{Methyl-[(R)-3-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-butyl]-carbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester (161708-51-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / Et₃N, DCC, DMAP / CH₂Cl₂ / 22 h / Ambient temperature

2: 98 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / 5 h / 2068.6 Torr

3: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH₂Cl₂, -15 deg C, 30 min, 2.) 0 deg C, 6 h

With 4-methyl-morpholine; dmap; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/jo00097a022

Reference yield:

Z-D-Leu-OH (28862-79-5) → (S)-2-{Methyl-[(R)-3-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-butyl]-carbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester (161708-51-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / KOH, Bu₄N(+)HSO₄(-) / tetrahydrofuran

2: 78 percent / Et₃N, DCC, DMAP / CH₂Cl₂ / 22 h / Ambient temperature

3: 98 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / 5 h / 2068.6 Torr

4: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH₂Cl₂, -15 deg C, 30 min, 2.) 0 deg C, 6 h

With 4-methyl-morpholine; dmap; potassium hydroxide; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/jo00097a022

Reference yield:

N-methyl-N-(benzyloxycarbonyl)-D-leucine (65635-85-0) → (S)-2-{Methyl-[(R)-3-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-butyl]-carbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester (161708-51-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / Et₃N, DCC, DMAP / CH₂Cl₂ / 22 h / Ambient temperature

2: 98 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / 5 h / 2068.6 Torr

3: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH₂Cl₂, -15 deg C, 30 min, 2.) 0 deg C, 6 h

With 4-methyl-morpholine; dmap; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/jo00097a022

upstream raw materials:

N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester

(S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-benzyl ester

2-(Trimethylsilyl)ethanol

Z-D-Leu-OH

Downstream raw materials:

C₆₂H₈₉N₇O₁₅

Cyclo<(N-L-prolyl-N-methyl-D-leucyl)-O-<oxy>-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl>

N-Cbz-3,4-didehydro-L-prolyl-N-methyl-D-leucine

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