Lithium Hydroxide → HCID 66770536, compound

HRID 1697635Notes

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]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:36](=[O:38])[CH3:37])[CH:30]=2)[N:25]=[C:26]([CH3:28])[CH:27]=1)=[O:4].COC([C@H]1C[C@@H](S(C2C=CC=CC=2C(F)(F)F)(=O)=O)CN1C1N(C2C=CC=C(NC(=O)C)C=2)N=C(C)C=1)=O.[OH-].[Li+].C(NC1C=C(N2C(N3C[C@H](S(C4C=CC=CC=4C(F)(F)F)(=O)=O)C[C@@H]3C(O)=O)=CC(C)=N2)C=CC=1)(=O)C>>[C:36]([NH:35][C:31]1[CH:30]=[C:29]([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:22])([F:20])[F:21])(=[O:12])=[O:11])[CH2:9][C@H:5]3[C:3]([OH:4])=[O:2])=[CH:27][C:26]([CH3:28])=[N:25]2)[CH:34]=[CH:33][CH:32]=1)(=[O:38])[CH3:37]

Participants

Reactant 4

HCID 3939Lithium Hydroxide

HCID 66771013HCID 66771013, compound

HCID 66771041HCID 66771041, compound

HCID 66771276HCID 66771276, compound

Product 1

HCID 66770536HCID 66770536, compound

Procedure

In analogy to the procedure described in example 253e, a mixture of (2S,4R)-1-[2-(3-acetylamino-phenyl)-5-methyl-2H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester and (2R,4R)-1-[2-(3-acetylamino-phenyl)-5-methyl-2H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was saponified in the presence of lithium hydroxide to give a mixture of the title compound and (2R,4R)-1-[2-(3-acetylamino-phenyl)-5-methyl-2H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid as orange solid which was used in the next step without further purification. MS (ESI): m/z=537.2 [M+H]+.

Workup

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Sources & evidence

ORD record: ord-1258e87b5e4c4092950ad9974d964ad0
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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