(3S,7R)-7-Acetoxymethyl-3-(benzyl-benzyloxycarbonyl-amino)-2-oxo-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3S,7R)-7-Acetoxymethyl-3-(benzyl-benzyloxycarbonyl-amino)-2-oxo-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester
CAS No.:815584-70-4
Molecular Formula:C₂₉H₃₄N₂O₇
Molecular Weight:522.598
Hs Code.:

Synonyms:(3S,7R)-7-Acetoxymethyl-3-(benzyl-benzyloxycarbonyl-amino)-2-oxo-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester

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Chemical Property of (3S,7R)-7-Acetoxymethyl-3-(benzyl-benzyloxycarbonyl-amino)-2-oxo-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester

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Technology Process of (3S,7R)-7-Acetoxymethyl-3-(benzyl-benzyloxycarbonyl-amino)-2-oxo-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester

There total 7 articles about (3S,7R)-7-Acetoxymethyl-3-(benzyl-benzyloxycarbonyl-amino)-2-oxo-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl 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: 99.0%

: 815584-69-1
(R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)amino-(N-tert-butoxycarbonyl)pent-4-enamido)but-3-enyl acetate

: 815584-70-4
(3S,7R)-7-Acetoxymethyl-3-(benzyl-benzyloxycarbonyl-amino)-2-oxo-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 2h; Heating;
DOI:10.1021/jo0485738

Reference yield:

: (S)-2-(Benzyl-benzyloxycarbonyl-amino)-pent-4-enoic acid methyl ester

: 815584-70-4
(3S,7R)-7-Acetoxymethyl-3-(benzyl-benzyloxycarbonyl-amino)-2-oxo-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 0.82 g / aq. NaOH / methanol / 3 h

2: PyBOP; Et₃N / CH₂Cl₂ / 16 h / 20 °C

3: 0.89 g / pyridine / CH₂Cl₂ / 1 h

4: 77 percent / DMAP / tetrahydrofuran / 20 h / 20 °C

5: 99 percent / Grubb's second-generation catalyst / CH₂Cl₂ / 2 h / Heating

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo0485738

Reference yield:

: 815584-68-0
(R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)aminopent-4-enamido)but-3-enyl acetate

: 815584-70-4
(3S,7R)-7-Acetoxymethyl-3-(benzyl-benzyloxycarbonyl-amino)-2-oxo-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 77 percent / DMAP / tetrahydrofuran / 20 h / 20 °C

2: 99 percent / Grubb's second-generation catalyst / CH₂Cl₂ / 2 h / Heating

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo0485738