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

HRID 1796772Notes

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 MgSO41 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
customThe extract was dried over anhydrous MgSO41
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-e7b0c53d875c46b793cb5fcca70cf6f1
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030120B2

Reaction notes

Loading…