Methanol → 4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)benzoic acid

HRID 1476334Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C@H:14]([NH:32][S@:33]([C:35]([CH3:38])([CH3:37])[CH3:36])=[O:34])[CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1.CO.[Li+].[OH-]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C@H:14]([NH:32][S@:33]([C:35]([CH3:38])([CH3:37])[CH3:36])=[O:34])[CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:31]=[CH:30][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 4-(4-((R)-(4′-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)benzoate (INTERMEDIATE 128, 0.40 g, 0.62 mmol) in THF (4.3 ml) was added MeOH (1.4 ml) and a solution of LiOH (0.09 g, 4.44 mmol) in water (1.4 ml). The reaction mixture was stirred at 40° C. overnight. The reaction mixture was cooled to rt, concentrated under reduced pressure, and the residue suspended in water. The suspension was cooled to 0° C., acidified to pH ˜2 using 1N HCl aq., filtered, and the filtercake dried in a vacuum oven to provide the title compound (0.38 g, yield: almost quantitative).

Workup

temperatureThe reaction mixture was cooled to rt
concentrationconcentrated under reduced pressure
temperatureThe suspension was cooled to 0° C.
filtrationfiltered
customthe filtercake dried in a vacuum oven

Sources & evidence

ORD record: ord-e3122e2404d94e4f8b6857e3be5a6427
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018381B2

Reaction notes

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