4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 168050-53-1
• Molecular Formula: C₄₀H₄₆N₄O₇S
• Molecular Weight: 726.894

Synonyms:

Chemical Property of 4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of 4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-carboxylic acid benzyl ester

There total 8 articles about 4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-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:

BOC-O-benzyl-L-serine (23680-31-1) → 4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-carboxylic acid benzyl ester (168050-53-1)

Guidance literature:

Multi-step reaction with 5 steps

1: EDAC; HOBt; NMM / dimethylformamide

2: TFA / CH₂Cl₂ / 0 °C

3: Et₃N / CH₂Cl₂

4: H₂ / 10 percent Pd/C / ethanol

5: EDAC; HOBt; NMM / dimethylformamide

With 4-methyl-morpholine; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00664-3

Reference yield:

(S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate (86661-32-7) → 4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-carboxylic acid benzyl ester (168050-53-1)

Guidance literature:

Multi-step reaction with 7 steps

1: NaN₃ / dimethylsulfoxide / 70 °C

2: TFA / CH₂Cl₂ / 0 °C

3: EDAC; HOBt; NMM / dimethylformamide

4: TFA / CH₂Cl₂ / 0 °C

5: Et₃N / CH₂Cl₂

6: H₂ / 10 percent Pd/C / ethanol

7: EDAC; HOBt; NMM / dimethylformamide

With 4-methyl-morpholine; sodium azide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00664-3

Reference yield:

tert-butyl (2S)-2-(azidomethyl)-1-pyrrolidinecarboxylate (168049-26-1) → 4-[({(S)-1-[(S)-3-Benzyloxy-2-(naphthalene-2-sulfonylamino)-propionyl]-pyrrolidin-2-ylmethyl}-carbamoyl)-methyl]-piperidine-1-carboxylic acid benzyl ester (168050-53-1)

Guidance literature:

Multi-step reaction with 6 steps

1: TFA / CH₂Cl₂ / 0 °C

2: EDAC; HOBt; NMM / dimethylformamide

3: TFA / CH₂Cl₂ / 0 °C

4: Et₃N / CH₂Cl₂

5: H₂ / 10 percent Pd/C / ethanol

6: EDAC; HOBt; NMM / dimethylformamide

With 4-methyl-morpholine; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00664-3

upstream raw materials:

2-(1-((benzyloxy)carbonyl)piperidin-4-yl)acetic acid

Naphthalene-2-sulfonic acid [(S)-2-((S)-2-aminomethyl-pyrrolidin-1-yl)-1-benzyloxymethyl-2-oxo-ethyl]-amide

BOC-O-benzyl-L-serine

(S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

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