(2S,4S)-1-{(2S,4S)-1-[(2S,4S)-1-(2,2-Dimethyl-propionyl)-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl]-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl}-4-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,4S)-1-{(2S,4S)-1-[(2S,4S)-1-(2,2-Dimethyl-propionyl)-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl]-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl}-4-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid benzyl ester
• CAS No.: 204914-99-8
• Molecular Formula: C₃₆H₄₉N₃O₁₁
• Molecular Weight: 699.799

Synonyms:(2S,4S)-1-{(2S,4S)-1-[(2S,4S)-1-(2,2-Dimethyl-propionyl)-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl]-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl}-4-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property of (2S,4S)-1-{(2S,4S)-1-[(2S,4S)-1-(2,2-Dimethyl-propionyl)-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl]-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl}-4-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (2S,4S)-1-{(2S,4S)-1-[(2S,4S)-1-(2,2-Dimethyl-propionyl)-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl]-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl}-4-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid benzyl ester

There total 11 articles about (2S,4S)-1-{(2S,4S)-1-[(2S,4S)-1-(2,2-Dimethyl-propionyl)-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl]-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl}-4-methoxycarbonylmethyl-pyrrolidine-2-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:

(2S,4S)-4-Methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (204914-90-9) → (2S,4S)-1-{(2S,4S)-1-[(2S,4S)-1-(2,2-Dimethyl-propionyl)-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl]-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl}-4-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid benzyl ester (204914-99-8)

Guidance literature:

Multi-step reaction with 6 steps

1: TFA / 0.5 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

3: 91 percent / H₂ / 10percent Pd/C / methanol

4: 1.) DIC, DMAP, HOBt, 2.) Et₃N / 1.) CH₂Cl₂, 0 deg C, 0.5 h, 2.) CH₂Cl₂, RT, 15 h

5: 100 percent / H₂ / 10percent Pd/C / methanol

6: 1.) DIC, DMAP, HOBt, 2.) Et₃N / 1.) CH₂Cl₂, 0 deg C, 0.5 h, 2.) CH₂Cl₂, RT, 15 h

With dmap; hydrogen; benzotriazol-1-ol; dacarbazine; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja972494e

Reference yield:

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate (113400-36-5,400626-71-3) → (2S,4S)-1-{(2S,4S)-1-[(2S,4S)-1-(2,2-Dimethyl-propionyl)-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl]-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl}-4-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid benzyl ester (204914-99-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) LHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h

2: 1.) Et₃BHLi, 2.) 30percent aq. H₂O₂ / 1.) THF, -78 deg C, 30 min, 2.) THF, 0 deg C, 20 min

3: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to RT, 2 h

4: PDC / dimethylformamide / 9 h / Ambient temperature

5: NaHCO₃ / dimethylformamide / 20 h / Ambient temperature

6: TFA / 0.5 h / Ambient temperature

7: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

8: 91 percent / H₂ / 10percent Pd/C / methanol

9: 1.) DIC, DMAP, HOBt, 2.) Et₃N / 1.) CH₂Cl₂, 0 deg C, 0.5 h, 2.) CH₂Cl₂, RT, 15 h

10: 100 percent / H₂ / 10percent Pd/C / methanol

11: 1.) DIC, DMAP, HOBt, 2.) Et₃N / 1.) CH₂Cl₂, 0 deg C, 0.5 h, 2.) CH₂Cl₂, RT, 15 h

With dmap; dipyridinium dichromate; hydrogen; dihydrogen peroxide; lithium triethylborohydride; sodium hydrogencarbonate; benzotriazol-1-ol; ozone; dacarbazine; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja972494e

Reference yield:

(2S,4R)-4-(3-Methyl-but-2-enyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (204914-85-2) → (2S,4S)-1-{(2S,4S)-1-[(2S,4S)-1-(2,2-Dimethyl-propionyl)-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl]-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl}-4-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid benzyl ester (204914-99-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) Et₃BHLi, 2.) 30percent aq. H₂O₂ / 1.) THF, -78 deg C, 30 min, 2.) THF, 0 deg C, 20 min

2: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to RT, 2 h

3: PDC / dimethylformamide / 9 h / Ambient temperature

4: NaHCO₃ / dimethylformamide / 20 h / Ambient temperature

5: TFA / 0.5 h / Ambient temperature

6: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

7: 91 percent / H₂ / 10percent Pd/C / methanol

8: 1.) DIC, DMAP, HOBt, 2.) Et₃N / 1.) CH₂Cl₂, 0 deg C, 0.5 h, 2.) CH₂Cl₂, RT, 15 h

9: 100 percent / H₂ / 10percent Pd/C / methanol

10: 1.) DIC, DMAP, HOBt, 2.) Et₃N / 1.) CH₂Cl₂, 0 deg C, 0.5 h, 2.) CH₂Cl₂, RT, 15 h

With dmap; dipyridinium dichromate; hydrogen; dihydrogen peroxide; lithium triethylborohydride; sodium hydrogencarbonate; benzotriazol-1-ol; ozone; dacarbazine; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja972494e

upstream raw materials:

(2S,4S)-1-[(2S,4S)-1-(2,2-Dimethyl-propionyl)-4-methoxycarbonylmethyl-pyrrolidine-2-carbonyl]-4-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

(2S,4S)-1-(2,2-Dimethyl-propionyl)-4-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid

(2S,4S)-4-(2-Oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

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