Chloroform → HCID 21914833, compound

HRID 2117931Notes

Reaction equation

[C:1]([NH:4][C:5]1[S:6][C:7]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18](OCC)=[O:19])=[CH:12][CH:11]=2)[N:9]=1)(=[O:3])[CH3:2].[BH4-].[Li+].[Cl-].[NH4+].C(Cl)(Cl)Cl>O1CCCC1>[OH:19][CH2:18][CH2:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=2[C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of ethyl(2E)-3-(4-{2-(acetylamino)-5-[4-(methylsulfonyl)phenyl]-1,3-thiazol-4-yl}phenyl)acrylate (306.5 mg) in tetrahydrofuran (3 ml) was added portionwise lithium borohydride (271 mg) at 0° C., and the mixture was stirred for 6.5 h at 20° C. The reaction mixture was poured into a mixture of saturated ammonium chloride aqueous solution (50 ml) and chloroform (50 ml) at 0° C. The organic layer was separeted, dried over maganesium sulfate and evaporarted to give a crude yellow solid (300 mg). The residue was purified by column chromatography over silica gel (80 ml) with hexane/ethyl acetate (1:2-1:5) as an eluent to give N-{4-[4-(3-hydroxypropyl)phenyl]-5-[4-(methylsulfonyl)phenyl]-1,3-thiazol-2-yl}acetamide as a pale yellow solid.

Workup

dry with materialdried over maganesium sulfate
customto give a crude yellow solid (300 mg)
customThe residue was purified by column chromatography over silica gel (80 ml) with hexane/ethyl acetate (1:2-1:5) as an eluent

Sources & evidence

ORD record: ord-01d44ece796443b4bf2ad0214ef7c3a2
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442715B2

Reaction notes

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