Hexafluoroacetone → 2-[(4S)-3-(3,3-dimethylbutyl)-5-oxo-2,2-bis(trifluoromethyl)-1,3-oxazolan-4-yl]acetic acid

HRID 23782

Reaction equation

HRID 23782 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([C:5]([F:8])([F:7])[F:6])=[O:4].[CH3:11][C:12]([CH3:25])([CH3:24])[CH2:13][CH2:14][NH:15][C@H:16]([C:21](O)=[O:22])[CH2:17][C:18]([OH:20])=[O:19]>O1CCOCC1>[CH3:11][C:12]([CH3:25])([CH3:24])[CH2:13][CH2:14][N:15]1[C@@H:16]([CH2:17][C:18]([OH:20])=[O:19])[C:21](=[O:22])[O:4][C:3]1([C:5]([F:8])([F:7])[F:6])[C:2]([F:10])([F:9])[F:1]

Participants

4

Reactant 2

HCID 12695HexafluoroacetoneHCID 9815811N-(3,3-Dimethylbutyl)-L-aspartic acid

Product 1

HCID 865842562-[(4S)-3-(3,3-dimethylbutyl)-5-oxo-2,2-bis(trifluoromethyl)-1,3-oxazolan-4-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A gas flow of hexafluoroacetone is blown at a moderate rate at room temperature onto an intensely stirred suspension of 10 mmol of N-(3,3-dimethylbutyl)-L-aspartic acid in 20 ml 1,4-dioxane. A clear solution is formed overnight. The solvent was removed in vacuo, and the oily residue was confirmed to be an almost quantitative amount of 2-[(4S)-3-(3,3-dimethylbutyl)-5-oxo-2,2-bis(trifluoromethyl)-1,3-oxazolan-4-yl]acetic acid by NMR.

Workup

  1. customA clear solution is formed overnight
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ba8cbbba95a141b3b065b8c63392d2a5
Source dataset
uspto-grants-2005_02
Patent number
US06852875B2

Linked notes

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