N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester

Base Information

• Chemical Name: N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester
• CAS No.: 357429-20-0
• Molecular Formula: C₃₅H₄₅N₅O₅Si
• Molecular Weight: 643.858

Synonyms:N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester

Chemical Property of N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester

Chemical Property:

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Technology Process of N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester

There total 5 articles about N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-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:

(S)-(2,5-dioxopyrrolidin-1-yl) 1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate (357429-08-4) + L-(benzyl)histidyl-L-proline benzyl ester hydrochloride → N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester (357429-20-0)

Guidance literature:

With triethylamine; In dichloromethane; at -10 - 20 ℃;

DOI:10.1002/1521-4184(200105)334:5<167::AID-ARDP167>3.3.CO;2-F

Reference yield:

(4S)-N-tert-butyldimethylsilylazetidin-2-one-4-carboxylic acid (82938-50-9,162856-35-1) → N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester (357429-20-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 25 h / -10 - 20 °C

2: 780 mg / Et₃N / CH₂Cl₂ / -10 - 20 °C

With triethylamine; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1002/1521-4184(200105)334:5<167::AID-ARDP167>3.3.CO;2-F

Reference yield:

Boc-His(Bzl)-OH (20898-44-6,81018-79-3) → N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester (357429-20-0)

Guidance literature:

Multi-step reaction with 4 steps

1: dicyclohexylcarbodiimide

2: 3.2 g / Et₃N / CH₂Cl₂ / -10 °C

3: HCl / ethyl acetate / 4 h / 0 - 20 °C

4: 780 mg / Et₃N / CH₂Cl₂ / -10 - 20 °C

With hydrogenchloride; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; ethyl acetate;

DOI:10.1002/1521-4184(200105)334:5<167::AID-ARDP167>3.3.CO;2-F

upstream raw materials:

(S)-(2,5-dioxopyrrolidin-1-yl) 1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

(4S)-N-tert-butyldimethylsilylazetidin-2-one-4-carboxylic acid

Boc-His(Bzl)-OH

N-(1-benzyl-N^α-tert-butoxycarbonyl-histidyloxy)-succinimide

Downstream raw materials:

N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester

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