1,3-Dibromo-2-propanone → HCID 59826674, compound

HRID 898855Notes

Reaction equation

[CH3:1][O:2][C:3]([C@:5]1([NH:15][S:16]([C:19]2[S:23][C:22]([NH2:24])=[N:21][CH:20]=2)(=[O:18])=[O:17])[CH2:7][C@:6]1([CH3:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[Br:25][CH2:26][C:27]([CH2:29]Br)=O>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C@:5]1([NH:15][S:16]([C:19]2[S:23][C:22]3=[N:24][C:27]([CH2:26][Br:25])=[CH:29][N:21]3[CH:20]=2)(=[O:18])=[O:17])[CH2:7][C@:6]1([CH3:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (1S,2R)-1-(2-amino-thiazol-5-sulfonylamino)-2-methyl-2-phenyl-cyclopropanecarboxylic acid methyl ester (0.21 g, 0.58 mmol) in ethyl acetate (6.4 mL) was added 1,3-dibromoacetone (0.18 mL, 0.87 mmol), and the mixture was stirred at 60° C. for 18 hours. After cooling to room temperature, the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, and dried over sodium sulfate. After filtration and evaporation, the obtained residue was separated and purified by silica gel chromatography (hexane:ethyl acetate=1:1) to give the title compound (68 mg, yield 24%) as a pale-yellow solid.

Workup

temperatureAfter cooling to room temperature
washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
filtrationAfter filtration and evaporation
customthe obtained residue was separated
custompurified by silica gel chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-9ae8b174f2674f559f22f383e38970c8
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351825B2

Reaction notes

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