Sodium Hydroxide → HCID 54148437, compound

HRID 612503Notes

Reaction equation

HRID 612503 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C@H:7]([C:9]([OH:11])=[O:10])[CH3:8])=[O:5].[OH-].[Na+].[F:19][C:20](=[C:24]([F:26])[F:25])[CH2:21][CH2:22]Br>CS(C)=O.O>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C@H:7]([C:9]([O:11][CH2:22][CH2:21][C:20]([F:19])=[C:24]([F:26])[F:25])=[O:10])[CH3:8])=[O:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 28122405HCID 28122405, compound

Product 1

HCID 54148437HCID 54148437, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

6.4 g (28 mmol) of N-(2,6-difluorobenzoyl)alanine are dissolved in 50 ml of dimethyl sulphoxide (DMSO) and admixed with 1.2 g (31 mmol) of sodium hydroxide dissolved in a little water. 5.7 g (30 mmol) of 3,4,4-trifluorobut-3-enyl bromide are subsequently added, and the mixture is stirred at 20° C. overnight. The mixture is then poured into water and the product is extracted with ethyl acetate and subsequently purified by column chromatography over silica gel using the system ethyl acetate. In this manner, 2.5 g (26.5% of theory) of 3,4,4-trifluorobut-3-enyl N-(2,6-difluorobenzoyl)-alaninate are obtained as an oil. log p (pH 2)=2.42.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. customsubsequently purified by column chromatography over silica gel using the system ethyl acetate

Sources & evidence

ORD record
ord-918bd8a489714441be3dc8671bc37b0f
Source dataset
uspto-grants-1999_12
Patent number
US06004992

Reaction notes

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