Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16](/[CH:20]=[CH:21]/[C:22]2[S:23][CH:24]=[C:25]([CH:27]3[CH2:30][CH2:29][CH2:28]3)[N:26]=2)[CH:15]=1)=[O:12].[BH4-].[Na+].O1CCCC1.CO>O>[CH:27]1([C:25]2[N:26]=[C:22](/[CH:21]=[CH:20]/[C:16]3[CH:15]=[C:14]([NH:13][C:11](=[O:12])[CH2:10][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[CH2:3][OH:2])[CH:19]=[CH:18][CH:17]=3)[S:23][CH:24]=2)[CH2:28][CH2:29][CH2:30]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 0.865 g of (E)-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid methyl ester, 0.5 g of sodium borohydride, 75 ml of tetrahydrofuran and 20 ml of methanol was stirred under a positive nitrogen atmosphere for 20 hr. The reaction mixture was condensed in vacuo and the residual materials were mixed with water and extracted with methylene chloride. The combined extracts were washed with water, dried (MgSO4) and condensed in vacuo. The residual materials were further purified by chromatography over florisil using ethyl acetate as the eluant to yield (E)-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzyl alcohol.
Workup
- customcondensed in vacuo
- extractionextracted with methylene chloride
- washThe combined extracts were washed with water
- customdried
- custom(MgSO4) and condensed in vacuo
- customThe residual materials were further purified by chromatography over florisil
Sources & evidence
- ORD record
- ord-8f7f02745634455e9e07cddbc96a0301
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05399702
Linked notes
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