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

HRID 1697675Notes

Reaction equation

HRID 1697675 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[N:24]([CH:34]2[CH2:37][CH2:36][CH2:35]2)[N:25]=[C:26]([CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:27]=1)=[O:4].[OH-].[Li+]>>[CH:34]1([N:24]2[C:23]([N:6]3[CH2:7][C@H:8]([S:10]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:19]([F:20])([F:22])[F:21])(=[O:11])=[O:12])[CH2:9][C@H:5]3[C:3]([OH:4])=[O:2])=[CH:27][C:26]([CH:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)=[N:25]2)[CH2:37][CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 67278244(2S,4R)-1-[2-Cyclobutyl-5-(tetrahydro-pyran-4-yl)-2H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 66770427(2S,4R)-1-[2-Cyclobutyl-5-(tetrahydro-pyran-4-yl)-2H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid

Procedure

In analogy to the procedure described in example 253e, (2S,4R)-1-[2-cyclobutyl-5-(tetrahydro-pyran-4-yl)-2H-pyrazol-3-yl]-4-(2-trifluorom ethyl-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=528.3 [M+H]+.

Sources & evidence

ORD record
ord-56a7b49626db48289a7143d9bfbb1961
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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