ethyl (2R,4S)-N-BOC-4-benzyl pyroglutamate

Base Information

• Chemical Name: ethyl (2R,4S)-N-BOC-4-benzyl pyroglutamate
• CAS No.: 474024-64-1
• Molecular Formula: C₁₉H₂₅NO₅
• Molecular Weight: 347.411
• Mol file: 474024-64-1.mol

Synonyms:ethyl (2R,4S)-N-BOC-4-benzyl pyroglutamate

Chemical Property of ethyl (2R,4S)-N-BOC-4-benzyl pyroglutamate

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of ethyl (2R,4S)-N-BOC-4-benzyl pyroglutamate

There total 1 articles about ethyl (2R,4S)-N-BOC-4-benzyl pyroglutamate 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: 60.0%

benzyl bromide (100-39-0) + 1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate (144978-12-1,128811-48-3,144978-35-8,251924-83-1) → ethyl (2R,4S)-N-BOC-4-benzyl pyroglutamate (474024-64-1)

Guidance literature:

1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

benzyl bromide; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1021/jm020901d

Reference yield: 90.0%

ethyl (2R,4S)-N-BOC-4-benzyl pyroglutamate (474024-64-1) → (2R,4S)-2-amino-4-benzyl pentanedioic acid hydrochloride

Guidance literature:

ethyl (2R,4S)-N-BOC-4-benzyl pyroglutamate; With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 2h;

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 1h;

DOI:10.1021/jm020901d

Reference yield:

ethyl (2R,4S)-N-BOC-4-benzyl pyroglutamate (474024-64-1) → (2S,4R)-2-Amino-4-benzyl-pentanedioic acid (402821-16-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2.5 N aq. LiOH / tetrahydrofuran / 2 h / 20 °C

1.2: 90 percent / HCl / ethyl acetate / 1 h / 20 °C

2.1: 70 percent / propylene oxide / methanol / 20 °C

With lithium hydroxide; methyloxirane; In tetrahydrofuran; methanol;

DOI:10.1021/jm020901d

upstream raw materials:

benzyl bromide

1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate

Downstream raw materials:

(2S,4R)-2-Amino-4-benzyl-pentanedioic acid