tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

Base Information

Chemical Name:tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate
CAS No.:847955-65-1
Molecular Formula:C₂₅H₃₅N₃O₆S
Molecular Weight:505.635
Hs Code.:

Synonyms:tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

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Chemical Property of tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

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Technology Process of tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

There total 2 articles about tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate 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:

: 746671-16-9
tert-butyl (1R,2S,5R)-2-amino-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

: 1152-62-1
Cbz-Met-OH

: 847955-65-1
tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

Guidance literature:: With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In DMF (N,N-dimethyl-formamide); at 0 - 20 ℃; for 12h;

Reference yield:

: 746670-91-7
(1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

: 847955-65-1
tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 36 h / 760.05 Torr

2: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / acetonitrile / 4 h / 20 °C

With palladium 10% on activated carbon; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In ethyl acetate; acetonitrile;
DOI:10.1021/acsmedchemlett.8b00439

Reference yield:

: 847955-65-1
tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

: 746671-17-0
tert-butyl (1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

Guidance literature:: tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate; With methyl iodide; at 20 ℃; for 12h;

With caesium carbonate; In DMF (N,N-dimethyl-formamide); for 12h;