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

Base Information

Chemical Name:N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester
CAS No.:357429-21-1
Molecular Formula:C₂₉H₃₁N₅O₅
Molecular Weight:529.596
Hs Code.:

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

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

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

There total 5 articles about N-{N-[(2S)-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: 22.0%

: 357429-20-0
N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester

: 357429-21-1
N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1002/1521-4184(200105)334:5<167::AID-ARDP167>3.3.CO;2-F

Reference yield:

: 20898-44-6,81018-79-3
Boc-His(Bzl)-OH

: 357429-21-1
N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 22 percent / Bu₄NF; glac. HOAc / tetrahydrofuran / 0.5 h / 0 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1002/1521-4184(200105)334:5<167::AID-ARDP167>3.3.CO;2-F

Reference yield:

: 21761-38-6
N-(1-benzyl-N^α-tert-butoxycarbonyl-histidyloxy)-succinimide

: 357429-21-1
N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-proline benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 3.2 g / Et₃N / CH₂Cl₂ / -10 °C

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

3: 780 mg / Et₃N / CH₂Cl₂ / -10 - 20 °C

4: 22 percent / Bu₄NF; glac. HOAc / tetrahydrofuran / 0.5 h / 0 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1002/1521-4184(200105)334:5<167::AID-ARDP167>3.3.CO;2-F