(2S,3S)-3-N-(tert-butoxycarbonyl)amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide

Base Information

Chemical Name:(2S,3S)-3-N-(tert-butoxycarbonyl)amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide
CAS No.:690258-06-1
Molecular Formula:C₂₇H₄₀BF₂N₃O₆
Molecular Weight:551.439
Hs Code.:

(2S,3S)-3-N-(tert-butoxycarbonyl)amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide

Synonyms:(2S,3S)-3-N-(tert-butoxycarbonyl)amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide

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Chemical Property of (2S,3S)-3-N-(tert-butoxycarbonyl)amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide

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Technology Process of (2S,3S)-3-N-(tert-butoxycarbonyl)amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide

There total 4 articles about (2S,3S)-3-N-(tert-butoxycarbonyl)amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide 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: 98.0%

: 690258-05-0
(2S,3S)-N-(tert-butoxycarbonyl)amino-2-(4-bromophenyl)-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxobutanamide

: 73183-34-3
bis(pinacol)diborane

: 690258-06-1
(2S,3S)-3-N-(tert-butoxycarbonyl)amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide

Guidance literature:: With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 90 ℃; for 12h;
DOI:10.1016/j.bmcl.2007.08.049

Reference yield:

: 899429-12-0
(2S,3S)-2-(4-Bromo-phenyl)-3-tert-butoxycarbonylamino-4-(3,3-difluoro-pyrrolidin-1-yl)-4-oxo-butyric acid

: 690258-06-1
(2S,3S)-3-N-(tert-butoxycarbonyl)amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide

Guidance literature:: Multi-step reaction with 2 steps

1: 11.53 g / HOBt; N,N-diisopropylethylamine; EDC / dimethylformamide; tetrahydrofuran / 12 h / 20 °C

2: 84 percent / [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂*CH₂Cl₂; AcOK / dimethylsulfoxide / 4 h / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm060015t

Reference yield:

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

: 690258-06-1
(2S,3S)-3-N-(tert-butoxycarbonyl)amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium permanganate; sodium periodate; potassium carbonate / water; tert-butyl alcohol / 24 h / 20 °C

1.2: 12 h / 20 °C

2.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 4.05 h / 80 °C

With potassium permanganate; sodium periodate; potassium acetate; potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In water; dimethyl sulfoxide; tert-butyl alcohol; 2.1: Suzuki Coupling;