(2S,3S,4E)-3-(4-bromophenyl)-1-(3,3-difluoropyrrolidin-1-yl)-1-oxohex-4-en-2-N-(tert-butoxycarbonyl)amine

Base Information

Chemical Name:(2S,3S,4E)-3-(4-bromophenyl)-1-(3,3-difluoropyrrolidin-1-yl)-1-oxohex-4-en-2-N-(tert-butoxycarbonyl)amine
CAS No.:690258-04-9
Molecular Formula:C₂₁H₂₇BrF₂N₂O₃
Molecular Weight:473.358
Hs Code.:

Synonyms:(2S,3S,4E)-3-(4-bromophenyl)-1-(3,3-difluoropyrrolidin-1-yl)-1-oxohex-4-en-2-N-(tert-butoxycarbonyl)amine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,4E)-3-(4-bromophenyl)-1-(3,3-difluoropyrrolidin-1-yl)-1-oxohex-4-en-2-N-(tert-butoxycarbonyl)amine

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Technology Process of (2S,3S,4E)-3-(4-bromophenyl)-1-(3,3-difluoropyrrolidin-1-yl)-1-oxohex-4-en-2-N-(tert-butoxycarbonyl)amine

There total 3 articles about (2S,3S,4E)-3-(4-bromophenyl)-1-(3,3-difluoropyrrolidin-1-yl)-1-oxohex-4-en-2-N-(tert-butoxycarbonyl)amine 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: 96.0%

: 690258-03-8
(βS)-4-bromo-N-(tert-butoxycarbonyl)-β-[(1E)-prop-1-en-1-yl]-L-phenylalanine

: 316131-01-8
3,3-difluoropyrrolidine

: 690258-04-9
(2S,3S,4E)-3-(4-bromophenyl)-1-(3,3-difluoropyrrolidin-1-yl)-1-oxohex-4-en-2-N-(tert-butoxycarbonyl)amine

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1021/jm060015t

Reference yield:

: 690257-98-8
methyl (βS)-4-bromo-N-(tert-butoxycarbonyl)-β-[(1E)-prop-1-enyl]-L-phenylalaninate

: 316131-01-8
3,3-difluoropyrrolidine

: 690258-04-9
(2S,3S,4E)-3-(4-bromophenyl)-1-(3,3-difluoropyrrolidin-1-yl)-1-oxohex-4-en-2-N-(tert-butoxycarbonyl)amine

Guidance literature:: methyl (βS)-4-bromo-N-(tert-butoxycarbonyl)-β-[(1E)-prop-1-enyl]-L-phenylalaninate; With sodium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 3h;

3,3-difluoropyrrolidine; With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 12h;

Reference yield:

: 690257-98-8
methyl (βS)-4-bromo-N-(tert-butoxycarbonyl)-β-[(1E)-prop-1-enyl]-L-phenylalaninate

: 690258-04-9
(2S,3S,4E)-3-(4-bromophenyl)-1-(3,3-difluoropyrrolidin-1-yl)-1-oxohex-4-en-2-N-(tert-butoxycarbonyl)amine

Guidance literature:: Multi-step reaction with 2 steps

1: aq. NaOH / methanol; tetrahydrofuran / 3 h / 20 °C

2: 96 percent / HOBt; N,N-diisopropylethylamine; EDC / dimethylformamide / 12 h / 20 °C

With sodium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jm060015t