2-((S)-1-{(S)-2-[(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: 2-((S)-1-{(S)-2-[(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester
• CAS No.: 404909-87-1
• Molecular Formula: C₃₈H₄₀N₄O₇S
• Molecular Weight: 696.824

Synonyms:2-((S)-1-{(S)-2-[(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester

Chemical Property of 2-((S)-1-{(S)-2-[(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2-((S)-1-{(S)-2-[(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester

There total 6 articles about 2-((S)-1-{(S)-2-[(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic 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:

2-[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carboxylic acid ethyl ester; hydrochloride + N-α-(9-fluorenylmethoxycarbonyl)-L-allo-threonine → 2-((S)-1-{(S)-2-[(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester (404909-87-1)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ja017160a

Reference yield:

(S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate (35150-07-3) → 2-((S)-1-{(S)-2-[(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester (404909-87-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 99 percent / Lawesson's reagent / tetrahydrofuran / 3.5 h / 20 °C

2.1: KHCO₃ / 1,2-dimethoxy-ethane / 0.5 h / 20 °C

2.2: 76 percent / trifluoroacetic anhydride; 2,6-lutidine / 0.5 h / 0 °C

3.1: HCl / dioxane; CH₂Cl₂ / 2 h / 20 °C

4.1: 647 mg / EDC; HOBT; N-methyl morpholine / CH₂Cl₂ / 0 - 20 °C

5.1: HCl / dioxane; CH₂Cl₂ / 2 h / 20 °C

6.1: 720 mg / EDC; HOBT; N-methyl morpholine / CH₂Cl₂ / 0 - 20 °C

With Lawessons reagent; 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; potassium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/ja017160a

Reference yield:

tert‐butyl (S)‐2‐carbamothioylpyrrolidine‐1‐carboxylate (117175-41-4,101410-18-8) → 2-((S)-1-{(S)-2-[(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester (404909-87-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: KHCO₃ / 1,2-dimethoxy-ethane / 0.5 h / 20 °C

1.2: 76 percent / trifluoroacetic anhydride; 2,6-lutidine / 0.5 h / 0 °C

2.1: HCl / dioxane; CH₂Cl₂ / 2 h / 20 °C

3.1: 647 mg / EDC; HOBT; N-methyl morpholine / CH₂Cl₂ / 0 - 20 °C

4.1: HCl / dioxane; CH₂Cl₂ / 2 h / 20 °C

5.1: 720 mg / EDC; HOBT; N-methyl morpholine / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; potassium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/ja017160a

upstream raw materials:

(S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate

tert‐butyl (S)‐2‐carbamothioylpyrrolidine‐1‐carboxylate

ethyl (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylate

2-[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carboxylic acid ethyl ester

Downstream raw materials:

2-(1-{2-[2-(2-{[1-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester

2-((S)-1-{(S)-2-[(2S,3S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester

2-((S)-1-{(S)-2-[(2S,3S)-2-((2S,3S)-2-{[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid

cyclo(-(S)-Phe-(S)-Pro-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-)

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