Diethanolamine → 1-{4-[5-(2-Fluorobiphenyl-4-yl)[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester 3,3-dimethyl-2-oxobutyl ester
Reaction equation
[CH3:1][C:2]([CH3:26])([CH3:25])[C:3](=[O:24])[CH2:4][O:5][C:6]([C:8]1([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:13][CH2:12]CN[CH2:9]1)=[O:7].[F:27][C:28]1[CH:33]=[C:32]([C:34]2[O:38][N:37]=[C:36]([C:39]3[CH:52]=[CH:51][C:42]([CH2:43][N:44]([CH2:48]CO)CCO)=[CH:41][CH:40]=3)[N:35]=2)[CH:31]=[CH:30][C:29]=1[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.N(CCO)CCO>>[CH3:25][C:2]([CH3:1])([CH3:26])[C:3](=[O:24])[CH2:4][O:5][C:6]([C:8]1([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[CH2:13][CH2:12][N:44]([CH2:43][C:42]2[CH:51]=[CH:52][C:39]([C:36]3[N:35]=[C:34]([C:32]4[CH:31]=[CH:30][C:29]([C:53]5[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=5)=[C:28]([F:27])[CH:33]=4)[O:38][N:37]=3)=[CH:40][CH:41]=2)[CH2:48][CH2:9]1)=[O:7]Participants
4
Reactant 3
Product 1
Procedure
Condensation of piperidine-3,3-dicarboxylic acid 3-benzyl 3-(3,3-dimethyl-2-oxobutyl)ester onto 3-(4-chloromethylphenyl)-5-(2-fluorobiphenyl-4-yl)[1,2,4]oxadiazole is performed as described in step II for the preparation of 2-[{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}(2-hydroxyethyl)amino]-ethanol, with piperidine-3,3-dicarboxylic acid 3-benzyl 3-(3,3-dimethyl-2-oxobutyl)ester replaced by diethanolamine. This procedures affords 1-{4-[5-(2-fluorobiphenyl-4-yl)[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester 3,3-dimethyl-2-oxobutyl ester.
Sources & evidence
- ORD record
- ord-388c0e713cb043caa135c08503ccca1a
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809539B2
Reaction notes
Loading…