2-Bromo-3-oxobutyric acid tert-butyl ester → 2-[(R)-3-(4-isopropyl-benzylcarbamoyl)-4-(4-trifluoromethyl-benzenesulfonyl)-piperazin-1-yl]-4-methyl-thiazole-5-carboxylic acid tert-butyl ester

HRID 908584Notes

Reaction equation

[CH:1]([C:4]1[CH:35]=[CH:34][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][N:16]([C:18](=[S:20])[NH2:19])[CH2:15][CH2:14][N:13]2[S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:36]([O:40][C:41](=[O:47])[CH:42](Br)[C:43](=O)[CH3:44])([CH3:39])([CH3:38])[CH3:37]>C(#N)C>[C:36]([O:40][C:41]([C:42]1[S:20][C:18]([N:16]2[CH2:15][CH2:14][N:13]([S:21]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:33])[F:32])=[CH:28][CH:29]=3)(=[O:22])=[O:23])[C@@H:12]([C:10](=[O:11])[NH:9][CH2:8][C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:35][CH:34]=3)[CH2:17]2)=[N:19][C:43]=1[CH3:44])=[O:47])([CH3:39])([CH3:38])[CH3:37]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the compound (250 mg) obtained in Example 4 and 2-bromo-3-oxobutyric acid tert-butyl ester (168 mg) in acetonitrile (1.25 ml) was stirred at 80° C. for 20 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by thin layer chromatography (ethyl acetate:n-hexane=2:3) to give the title compound (268 mg).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by thin layer chromatography (ethyl acetate:n-hexane=2:3)

Sources & evidence

ORD record: ord-21c10a0ae3194acdb6a940bc806c4331
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017612B2

Reaction notes

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