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

Base Information

• Chemical Name: N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester
• CAS No.: 357429-22-2
• Molecular Formula: C₄₄H₅₄N₆O₆Si
• Molecular Weight: 791.035
• Mol file: 357429-22-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine 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-prolyl-L-phenylalanine benzyl ester hydrochloride → N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester (357429-22-2)

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:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester (357429-22-2)

Guidance literature:

Multi-step reaction with 6 steps

1: dicyclohexylcarbodiimide

2: 3.3 g / Et₃N / CH₂Cl₂ / -10 °C

3: HCl / ethyl acetate

4: 2.75 g / Et₃N / CH₂Cl₂ / -10 °C

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

6: 1.7 g / 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

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-prolyl-L-phenylalanine benzyl ester (357429-22-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 1.7 g / 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

upstream raw materials:

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

1-(tert-butoxycarbonyl)-L-proline

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

tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester

Downstream raw materials:

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