(2S,4S)-1-Acetyl-4-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-ylmethylsulfanyl)-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester

Base Information

Chemical Name:(2S,4S)-1-Acetyl-4-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-ylmethylsulfanyl)-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester
CAS No.:136175-18-3
Molecular Formula:C₂₃H₃₁N₃O₇S
Molecular Weight:493.581
Hs Code.:

Synonyms:(2S,4S)-1-Acetyl-4-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-ylmethylsulfanyl)-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester

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Chemical Property of (2S,4S)-1-Acetyl-4-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-ylmethylsulfanyl)-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester

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Technology Process of (2S,4S)-1-Acetyl-4-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-ylmethylsulfanyl)-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester

There total 16 articles about (2S,4S)-1-Acetyl-4-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-ylmethylsulfanyl)-pyrrolidine-2-carboxylic acid 4-nitro-phenyl 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: 32.0%

: 100-02-7,78813-13-5,89830-32-0
4-nitro-phenol

: 136175-11-6
(2S,4S)-1-Acetyl-4-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-ylmethylsulfanyl)-pyrrolidine-2-carboxylic acid

: 136175-18-3
(2S,4S)-1-Acetyl-4-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-ylmethylsulfanyl)-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester

Guidance literature:: With dicyclohexyl-carbodiimide; In ethyl acetate; at 0 - 23 ℃; for 15h;
DOI:10.1021/jo00023a037

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 136175-18-3,136175-19-4
(2S,4S)-1-Acetyl-4-(1-tert-butoxycarbonyl-pyrrolidin-2-ylmethylsulfanyl)-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 78 percent / NaHCO₃ / dioxane; H₂O / 2 h / 23 °C

2: 64 percent / pyridine / 15 h / 0 °C

3: 82 percent / 1M NaOH / methanol / 0 - 23 °C

4: 1) Na metal / 1) EtOH, 30 deg C, 2) DMSO, 16 h

5: NH₃, Na / 0.5 h / -78 °C

6: dimethylsulfoxide / 18 h / 23 °C

7: dicyclohexylcarbodiimide (DCCI) / ethyl acetate / 15 h / 0 - 23 °C

With pyridine; sodium hydroxide; ammonia; sodium; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; methanol; water; dimethyl sulfoxide; ethyl acetate;
DOI:10.1021/jo00023a037

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 136175-18-3
(2S,4S)-1-Acetyl-4-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-ylmethylsulfanyl)-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 78 percent / NaHCO₃ / dioxane; H₂O / 2 h / 23 °C

2: 64 percent / pyridine / 15 h / 0 °C

3: 82 percent / 1M NaOH / methanol / 0 - 23 °C

4: 1) Na metal / 1) EtOH, 30 deg C, 2) DMSO, 16 h

5: NH₃, Na / 0.5 h / -78 °C

6: 94 percent / dimethylsulfoxide / 18 h / 23 °C

7: 32 percent / dicyclohexylcarbodiimide (DCCI) / ethyl acetate / 15 h / 0 - 23 °C

With pyridine; sodium hydroxide; ammonia; sodium; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; methanol; water; dimethyl sulfoxide; ethyl acetate;
DOI:10.1021/jo00023a037