Lithium Hydroxide → HCID 57899070, compound

HRID 1404264Notes

Reaction equation

HRID 1404264 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][S:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)(=[O:26])=[O:25])=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[Li+].[OH-]>C1COCC1.CO.O>[F:36][C:33]([F:34])([F:35])[C:30]1[CH:29]=[CH:28][C:27]([S:24]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([C:14]3[CH:15]=[CH:16][C:11]([CH:8]4[CH2:7][CH2:6][CH:5]([CH2:4][C:3]([OH:37])=[O:2])[CH2:10][CH2:9]4)=[CH:12][CH:13]=3)=[N:18][CH:19]=2)(=[O:26])=[O:25])=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66615794(4-{4-[5-(4-Trifluoromethyl-benzenesulfonylamino)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Product 1

HCID 57899070HCID 57899070, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 0.136 g (0.256 mmol) of (4-{4-[5-(4-Trifluoromethyl-benzenesulfonylamino)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester in THF/MeOH (4:1) was added 0.500 mL of LiOH (4 M) and let stir at r.t. for 72 h. Removed solvent in vacuo. The residue was taken up in water, brought to pH 4 and the solid filtered to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20-1.31 (m, 2 H) 1.55-1.66 (m, 2 H) 1.81-1.89 (m, 1 H) 1.92-1.97 (m, 4 H) 2.27 (d, J=6.82 Hz, 2 H) 7.43 (d, J=8.34 Hz, 2 H) 7.69 (dd, J=8.59, 2.78 Hz, 1 H) 7.97 (d, J=8.59 Hz, 1 H) 8.02 (d, J=8.34 Hz, 2 H) 8.12 (m, 4 H) 8.47 (d, J=0.51 Hz, 1 H) 10.96 (br. s., 1 H) 12.13 (br. s., 1 H); (M+H)+=519.1.

Workup

  1. filtrationthe solid filtered

Sources & evidence

ORD record
ord-954ee17e11694a98b6d165ba9a52f59a
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

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