4-(5-methyl-4-phenyl-1H-pyrazol-3(2H)-on-2-yl)-piperidine → alpha-(R)-(3-(S)-((4-(5-methyl-4-phenyl-1H-pyrazol-3(2H)-on-2-yl)-piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

HRID 1068185Notes

Reaction equation

HRID 1068185 reaction equation
[CH3:1][C:2]1[NH:6][N:5]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[C:4](=[O:13])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:20][O:21][C:22]1[CH:51]=[CH:50][C:25]([CH2:26][O:27][C:28](=[O:49])[C@H:29]([N:36]2[CH2:40][C@H:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C@@H:38]([CH:47]=O)[CH2:37]2)[CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:24][CH:23]=1>>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][O:27][C:28](=[O:49])[C@H:29]([N:36]2[CH2:40][C@H:39]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C@@H:38]([CH2:47][N:10]3[CH2:9][CH2:8][CH:7]([N:5]4[C:4](=[O:13])[C:3]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)=[C:2]([CH3:1])[NH:6]4)[CH2:12][CH2:11]3)[CH2:37]2)[CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)=[CH:50][CH:51]=1

Participants

3

Reactant 2

HCID 211930114-(5-methyl-4-phenyl-1H-pyrazol-3(2H)-on-2-yl)-piperidineHCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 70124430alpha-(R)-(3-(S)-((4-(5-methyl-4-phenyl-1H-pyrazol-3(2H)-on-2-yl)-piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl esterYield 91.3%

Procedure

When 0.070 g of 4-(5-methyl-4-phenyl-1H-pyrazol-3(2H)-on-2-yl)-piperidine and 0.043 g of α-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester were used in the procedure of Example 124, Step C, there was obtained 0.061 g of α-(R)-(3-(S)-((4-(5-methyl-4-phenyl-1H-pyrazol-3(2H)-on-2-yl)-piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester after chromatography on silica gel (20 mL column—elution with 3% MeOH in dichlormethane). ESI-MS 677.3 (M+H); TPLC A: 2.85 min.

Sources & evidence

ORD record
ord-0b85417fe1da426085864649546039b0
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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