1-[2(R)-(2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl)pentanoyl]proline benzyl ester

Base Information

• Chemical Name: 1-[2(R)-(2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl)pentanoyl]proline benzyl ester
• CAS No.: 760187-86-8
• Molecular Formula: C₂₂H₂₉NO₆
• Molecular Weight: 403.475

Synonyms:1-[2(R)-(2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl)pentanoyl]proline benzyl ester

Chemical Property of 1-[2(R)-(2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl)pentanoyl]proline benzyl ester

Chemical Property:

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Technology Process of 1-[2(R)-(2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl)pentanoyl]proline benzyl ester

There total 2 articles about 1-[2(R)-(2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl)pentanoyl]proline 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: 78.0%

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) + 2(R)-(2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl)pentanoic acid (760187-85-7) → 1-[2(R)-(2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl)pentanoyl]proline benzyl ester (760187-86-8)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 18h;

DOI:10.1021/ja0489240

Reference yield:

2(R)-[2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl]pent-4-enoic acid (230962-23-9) → 1-[2(R)-(2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl)pentanoyl]proline benzyl ester (760187-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd/C / methanol / 20 °C

2: 78 percent / PYBOP; 1-hydroxy-7-azabenzotriazole; DIPEA / dimethylformamide / 18 h

With 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja0489240

Reference yield:

1-[2(R)-(2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl)pentanoyl]proline benzyl ester (760187-86-8) → (S)-1-[(R)-2-((S)-Carboxy-hydroxy-methyl)-pentanoyl]-pyrrolidine-2-carboxylic acid benzyl ester

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; tert-butyl alcohol; at 4 ℃;

DOI:10.1021/ja0489240

upstream raw materials:

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

2(R)-(2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl)pentanoic acid

2(R)-[2,2-dimethyl-5-oxo-(1,3)dioxolan-4(S)-yl]pent-4-enoic acid

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