Ethanamine, 2,2,2-trifluoro- → (2S,3S)-3-Amino-2-hydroxy-N-(2,2,2-trifluoroethyl)hexanamide

HRID 1025312Notes

Reaction equation

N[C@@H](CC)[C@H](O)[C:4](NC1CC1)=[O:5].[NH2:13][C@@H:14]([CH2:18][CH2:19][CH3:20])[C:15]([OH:17])=O.[F:21][C:22]([F:26])([F:25])[CH2:23][NH2:24]>>[NH2:13][C@@H:14]([CH2:18][CH2:19][CH3:20])[C@H:15]([OH:17])[C:4]([NH:24][CH2:23][C:22]([F:26])([F:25])[F:21])=[O:5]

Participants

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-

HCID 65098L-Norvaline

HCID 57872123(2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide

Product 1

HCID 86762421(2S,3S)-3-Amino-2-hydroxy-N-(2,2,2-trifluoroethyl)hexanamide

Procedure

The title compound was prepared in analogy to (2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide, Representative Procedure B, using (S)-2-aminopentanoic acid in the first step (step B1), and 2,2,2-trifluoro-ethylamine in the seventh step (step B7).

Sources & evidence

ORD record: ord-bbd88f2bfdc04cbe827c3819a7a18584
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729061B2

Reaction notes

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