(1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-5-((tertbutoxycarbonyl)amino)cyclohexane-1-carboxylic acid

Base Information

Chemical Name:(1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-5-((tertbutoxycarbonyl)amino)cyclohexane-1-carboxylic acid
CAS No.:1004536-61-1
Molecular Formula:C₂₄H₃₃N₃O₇
Molecular Weight:475.542
Hs Code.:

Synonyms:(1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-5-((tertbutoxycarbonyl)amino)cyclohexane-1-carboxylic acid

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Chemical Property of (1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-5-((tertbutoxycarbonyl)amino)cyclohexane-1-carboxylic acid

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Technology Process of (1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-5-((tertbutoxycarbonyl)amino)cyclohexane-1-carboxylic acid

There total 5 articles about (1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-5-((tertbutoxycarbonyl)amino)cyclohexane-1-carboxylic acid 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: 93.0%

: 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

: 1004536-61-1
(1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-5-((tertbutoxycarbonyl)amino)cyclohexane-1-carboxylic acid

Guidance literature:: 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; With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃;

With hydrogenchloride; sodium dihydrogenphosphate; In tetrahydrofuran; water; pH=~ 4;

Reference yield:

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

: 1004536-61-1
(1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-5-((tertbutoxycarbonyl)amino)cyclohexane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

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

2: 48 h / 20 °C

3: caesium carbonate / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere

4: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C

With lithium hydroxide monohydrate; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; dimethyl sulfoxide; acetonitrile;
DOI:10.1021/acsmedchemlett.8b00439

Reference yield:

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

: 1004536-61-1
(1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-5-((tertbutoxycarbonyl)amino)cyclohexane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 5 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

3: 48 h / 20 °C

4: caesium carbonate / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere

5: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C

With lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; dimethyl sulfoxide; ethyl acetate; acetonitrile;
DOI:10.1021/acsmedchemlett.8b00439