Water → 4-[10-Oxo-9-(2,2,2-trifluoroethylcarbamoyl)-9,10-dihydro-10lambda4-thioxanthen-9-yl]butyl bromide

HRID 1836841Notes

Reaction equation

[F:1][C:2]([F:27])([F:26])[CH2:3][NH:4][C:5]([C:7]1([CH2:21][CH2:22][CH2:23][CH2:24][Br:25])[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6].ClC1C=CC=C(C(OO)=[O:36])C=1.O>ClCCl>[O:36]=[S:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]([CH2:21][CH2:22][CH2:23][CH2:24][Br:25])([C:5](=[O:6])[NH:4][CH2:3][C:2]([F:1])([F:26])[F:27])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

The compound (46 mg) prepared in step (d) of Example 133 was dissolved in dichloromethane (1 ml). m-Chloroperbenzoic acid (19 mg) was added to the solution at 0° C., and the mixture was stirred at 0° C. for one hr. Water was added to the reaction solution, and the mixture was extracted with chloroform. The extract was dried over anhydrous MgSO4, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by preparative TLC (n-hexane:ethyl acetate=1:4) to give 4-[10-oxo-9-(2,2,2-trifluoroethylcarbamoyl)-9,10-dihydro-10λ4-thioxanthen-9-yl]butyl bromide (38 mg).

Workup

extractionthe mixture was extracted with chloroform
dry with materialThe extract was dried over anhydrous MgSO4
customthe solvent was then removed by distillation under the reduced pressure
customThe residue was purified by preparative TLC (n-hexane:ethyl acetate=1:4)

Sources & evidence

ORD record: ord-2afbded9a8f54ba9aca990363cbc83fe
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777414B1

Reaction notes

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