Lithium Hydroxide → (2S,4R)-1-[1-Methyl-5-(tetrahydro-pyran-4-yl)-1H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid

HRID 1697669Notes

Reaction equation

HRID 1697669 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11])[CH2:7][N:6]1[C:23]1[CH:27]=[C:26]([CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[N:25]([CH3:34])[N:24]=1)=[O:4].[OH-].[Li+]>>[CH3:34][N:25]1[C:26]([CH:28]2[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2)=[CH:27][C:23]([N:6]2[CH2:7][C@H:8]([S:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:21])([F:22])[F:20])(=[O:12])=[O:11])[CH2:9][C@H:5]2[C:3]([OH:4])=[O:2])=[N:24]1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 66772551(2S,4R)-1-[1-Methyl-5-(tetrahydro-pyran-4-yl)-1H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66772230(2S,4R)-1-[1-Methyl-5-(tetrahydro-pyran-4-yl)-1H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-1-[1-methyl-5-(tetrahydro-pyran-4-yl)-1H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide to give the title compound as yellow oil which was used in the next step without further purification. MS (ESI): m/z=488.3 [M+H]+.

Sources & evidence

ORD record
ord-289951a935ad4abb82339dce90874532
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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