Lithium Hydroxide → 4-{5-[(2S,4R)-2-Carboxy-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidin-1-yl]-3-methyl-pyrazol-1-yl}-piperidine-1-carboxylic Acid Benzyl Ester

HRID 1697692Notes

Reaction equation

HRID 1697692 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:21]([N:22]3[CH2:26][C@H:25]([S:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]([F:39])([F:38])[F:37])(=[O:29])=[O:28])[CH2:24][C@H:23]3[C:40]([O:42]C)=[O:41])=[CH:20][C:19]([CH3:44])=[N:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([N:17]2[C:21]([N:22]3[CH2:26][C@H:25]([S:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]([F:37])([F:38])[F:39])(=[O:29])=[O:28])[CH2:24][C@H:23]3[C:40]([OH:42])=[O:41])=[CH:20][C:19]([CH3:44])=[N:18]2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 667703984-{5-[(2S,4R)-2-Methoxycarbonyl-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidin-1-yl]-3-methyl-pyrazol-1-yl}-piperidine-1-carboxylic Acid Benzyl Ester

Product 1

HCID 667711964-{5-[(2S,4R)-2-Carboxy-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidin-1-yl]-3-methyl-pyrazol-1-yl}-piperidine-1-carboxylic Acid Benzyl Ester

Procedure

In analogy to the procedure described in example 253e, 4-{5-[(2S,4R)-2-methoxycarbonyl-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidin-1-yl]-3-methyl-pyrazol-1-yl}-piperidine-1-carboxylic acid benzyl ester was saponified in the presence of lithium hydroxide to give the title compound as yellow solid. MS (ESI): m/z=619.4 [M−H]−.

Sources & evidence

ORD record
ord-d8fa13b0f20741a0b234ffdf08a46876
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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