(S)-1-[(S)-1-((S)-2-{[(S)-2-((S)-2-Dimethylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-1-[(S)-1-((S)-2-{[(S)-2-((S)-2-Dimethylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid benzyl ester
• CAS No.: 215393-56-9
• Molecular Formula: C₃₅H₅₅N₅O₆
• Molecular Weight: 641.852

Synonyms:(S)-1-[(S)-1-((S)-2-{[(S)-2-((S)-2-Dimethylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property of (S)-1-[(S)-1-((S)-2-{[(S)-2-((S)-2-Dimethylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (S)-1-[(S)-1-((S)-2-{[(S)-2-((S)-2-Dimethylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid benzyl ester

There total 12 articles about (S)-1-[(S)-1-((S)-2-{[(S)-2-((S)-2-Dimethylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-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:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + TFA*H-Val-Val-MeVal-Pro-Pro-OBzl → (S)-1-[(S)-1-((S)-2-{[(S)-2-((S)-2-Dimethylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid benzyl ester (215393-56-9)

Guidance literature:

With triethylamine; palladium on activated charcoal; In methanol; water; at 20 ℃;

DOI:10.1016/S0040-4020(00)00657-8

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → (S)-1-[(S)-1-((S)-2-{[(S)-2-((S)-2-Dimethylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid benzyl ester (215393-56-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / 2-fluoro-1-ethylpyridinium tetrafluoroborate; DIEA / CH₂Cl₂ / 1 h / 20 °C

2: 94.7 percent / 4N HCl / ethyl acetate / 0 °C

3: 88 percent / 2-bromo-1-ethylpyridinium tetrafluoroborate; DIEA / CH₂Cl₂ / 20 °C

4: CH₂Cl₂

5: NEt₃ / Pd/C / methanol; H₂O / 20 °C

With hydrogenchloride; 2-fluoro-1-ethylpyridinium tetrafluoroborate; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; water; ethyl acetate; 1: Acylation / 2: Hydrolysis / 3: Acylation / 4: Substitution / 5: reductive methylation;

DOI:10.1016/S0040-4020(00)00657-8

Reference yield:

N-tert-butoxycarbonyl-L-valine methyl ester (58561-04-9) → (S)-1-[(S)-1-((S)-2-{[(S)-2-((S)-2-Dimethylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid benzyl ester (215393-56-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 4N HCl / ethyl acetate

2: 92.1 percent / 2-fluoro-1-ethylpyridinium tetrafluoroborate; DIEA / CH₂Cl₂ / 2 h / 20 °C

3: 91.4 percent / 4N HCl / ethyl acetate

4: 97 percent / 2-bromo-1-ethylpyridinium tetrafluoroborate; DIEA / CH₂Cl₂ / 1 h / 20 °C

5: 98 percent / 2N NaOH

6: 88 percent / 2-bromo-1-ethylpyridinium tetrafluoroborate; DIEA / CH₂Cl₂ / 20 °C

7: CH₂Cl₂

8: NEt₃ / Pd/C / methanol; H₂O / 20 °C

With hydrogenchloride; sodium hydroxide; 2-fluoro-1-ethylpyridinium tetrafluoroborate; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; water; ethyl acetate; 1: Substitution / 2: Acylation / 3: Substitution / 4: Acylation / 5: Hydrolysis / 6: Acylation / 7: Substitution / 8: reductive methylation;

DOI:10.1016/S0040-4020(00)00657-8

upstream raw materials:

formaldehyd

1-(tert-butoxycarbonyl)-L-proline

N-tert-butoxycarbonyl-L-valine methyl ester

methyl N-methyl-L-valinate hydrochloride

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