{(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester
• CAS No.: 686781-16-8
• Molecular Formula: C₂₄H₃₈N₄O₅S
• Molecular Weight: 494.656

Synonyms:{(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester

Chemical Property of {(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester

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Technology Process of {(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester

There total 8 articles about {(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic 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: 77.0%

(S)-5-[(S)-1-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-ylmethyl]-4-isobutyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidine-2-carboxylic acid tert-butyl ester (686781-15-7) → {(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester (686781-16-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2003.10.059

Reference yield:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) → {(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester (686781-16-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / N,N-diisopropylethylamine; N-hydroxybenzotriazole hydrate; EDCI / dimethylformamide / 11 h / 20 °C

2: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / cooling

3: 24.8 g / sodium (triacetoxy)borohydride; AcOH / 4 h / 20 °C

4: 80 percent / triethylamine / CH₂Cl₂ / 3.5 h

5: 58 percent / lithium borohydride / tetrahydrofuran; ethanol / 24 h / 20 °C

6: 95 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 3 h / 20 °C

7: 77 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

With lithium borohydride; oxalyl dichloride; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2003.10.059

Reference yield:

Cbz-L-Val-L-propinal (91650-00-9) → {(S)-1-[(S)-2-((S)-3-Isobutyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-ylmethyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester (686781-16-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 24.8 g / sodium (triacetoxy)borohydride; AcOH / 4 h / 20 °C

2: 80 percent / triethylamine / CH₂Cl₂ / 3.5 h

3: 58 percent / lithium borohydride / tetrahydrofuran; ethanol / 24 h / 20 °C

4: 95 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 3 h / 20 °C

5: 77 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

With lithium borohydride; sodium tris(acetoxy)borohydride; acetic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/j.bmc.2003.10.059

upstream raw materials:

(S)-5-[(S)-1-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-ylmethyl]-4-isobutyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidine-2-carboxylic acid tert-butyl ester

(S)-N-(benzyloxycarbonyl)valine

Cbz-L-Val-L-propinal

(S)-1-Pyrrolidin-2-yl-methanol

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