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

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Chemical Name:N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester
CAS No.:357429-23-3
Molecular Formula:C₃₈H₄₀N₆O₆
Molecular Weight:676.772
Hs Code.:

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

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

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

There total 9 articles about N-{N-[(2S)-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: 62.0%

: 357429-22-2
N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester

: 357429-23-3
N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine 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:

: 15761-39-4,59433-50-0
1-(tert-butoxycarbonyl)-L-proline

: 357429-23-3
N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester

Guidance literature:: Multi-step reaction with 7 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

7: 62 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:

: 3392-10-7
tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester

: 357429-23-3
N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 3.3 g / Et₃N / CH₂Cl₂ / -10 °C

2: HCl / ethyl acetate

3: 2.75 g / Et₃N / CH₂Cl₂ / -10 °C

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

5: 1.7 g / Et₃N / CH₂Cl₂ / -10 - 20 °C

6: 62 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