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

Base Information

• Chemical Name: 1-(2-{[2-(1-{2-[2-(2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carbonyl]-amino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 358624-95-0
• Molecular Formula: C₄₇H₆₃N₇O₁₀S
• Molecular Weight: 918.124

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 22 articles about 1-(2-{[2-(1-{2-[2-(2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carbonyl]-amino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl 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:

Boc-L-Pro-H (69610-41-9,117625-90-8) → 1-(2-{[2-(1-{2-[2-(2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carbonyl]-amino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester (358624-95-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 758 mg / triethylamine / toluene / 0 - 20 °C

2: 51 percent / chemical manganese dioxide / molecular sieves 4 Angstroem / benzene / 2 h / Heating

3: HCl / dioxane; H₂O / 0.33 h / 20 °C

4: 2.492 g / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 8 h / 0 - 20 °C

5: 4N aq. HCl / dioxane / 0.33 h / 20 °C

6: 1.581 g / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 8 h / 0 - 20 °C

7: HCl / methanol; dioxane; H₂O / 0.33 h / 20 °C

8: 1.399 g / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 7 h / 0 - 20 °C

9: LiOH / H₂O; tetrahydrofuran / 1 h / 0 - 20 °C

10: 574 mg / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 19.5 h / 0 - 20 °C

With hydrogenchloride; manganese(IV) oxide; lithium hydroxide; diethyl cyanophosphonate; triethylamine; 4 A molecular sieve; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4020(02)00906-7

Reference yield:

(2S)-2-(1-tert-butoxycarbonylpyrrolidin-2-yl)-thiazolidine-4-carboxylic acid methyl ester (347191-31-5) → 1-(2-{[2-(1-{2-[2-(2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carbonyl]-amino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester (358624-95-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 51 percent / chemical manganese dioxide / molecular sieves 4 Angstroem / benzene / 2 h / Heating

2: HCl / dioxane; H₂O / 0.33 h / 20 °C

3: 2.492 g / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 8 h / 0 - 20 °C

4: 4N aq. HCl / dioxane / 0.33 h / 20 °C

5: 1.581 g / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 8 h / 0 - 20 °C

6: HCl / methanol; dioxane; H₂O / 0.33 h / 20 °C

7: 1.399 g / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 7 h / 0 - 20 °C

8: LiOH / H₂O; tetrahydrofuran / 1 h / 0 - 20 °C

9: 574 mg / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 19.5 h / 0 - 20 °C

With hydrogenchloride; manganese(IV) oxide; lithium hydroxide; diethyl cyanophosphonate; triethylamine; 4 A molecular sieve; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(02)00906-7

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → 1-(2-{[2-(1-{2-[2-(2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carbonyl]-amino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid methyl ester (358624-95-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 88 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 14 h / 0 - 12 °C

2: LiAlH₄ / diethyl ether / 0.25 h / 0 °C

3: 758 mg / triethylamine / toluene / 0 - 20 °C

4: 51 percent / chemical manganese dioxide / molecular sieves 4 Angstroem / benzene / 2 h / Heating

5: HCl / dioxane; H₂O / 0.33 h / 20 °C

6: 2.492 g / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 8 h / 0 - 20 °C

7: 4N aq. HCl / dioxane / 0.33 h / 20 °C

8: 1.581 g / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 8 h / 0 - 20 °C

9: HCl / methanol; dioxane; H₂O / 0.33 h / 20 °C

10: 1.399 g / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 7 h / 0 - 20 °C

11: LiOH / H₂O; tetrahydrofuran / 1 h / 0 - 20 °C

12: 574 mg / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 19.5 h / 0 - 20 °C

With hydrogenchloride; manganese(IV) oxide; lithium hydroxide; lithium aluminium tetrahydride; diethyl cyanophosphonate; triethylamine; 4 A molecular sieve; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4020(02)00906-7

upstream raw materials:

(1S)-methyl 2-[(S)-2-amino-3-phenylpropanoyl]cyclopentanecarboxylate

1-(tert-butoxycarbonyl)-L-proline

N-tert-butoxycarbonyl-L-phenylalanine

Boc-L-Pro-H

Downstream raw materials:

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

cis,cis-Ceratospongamide

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