(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

Base Information

• Chemical Name: (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
• CAS No.: 686781-15-7
• Molecular Formula: C₂₉H₄₆N₄O₇S
• Molecular Weight: 594.773

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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: 95.0%

C29H48N4O8S (686781-14-6) → (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)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2003.10.059

Reference yield:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) → (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)

Guidance literature:

Multi-step reaction with 6 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

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; 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)-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)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1016/j.bmc.2003.10.059

upstream raw materials:

C₂₉H₄₈N₄O₈S

(S)-N-(benzyloxycarbonyl)valine

Cbz-L-Val-L-propinal

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

Downstream raw materials:

{(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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