Hydrochloric Acid → {(3S)-1-[5-(adamantan-1-ylcarbamoyl)-6-(propylthio)pyridin-2-yl]piperidin-3-yl}acetic acid

HRID 1187374Notes

Reaction equation

[OH-].[Li+].[C:3]12([NH:13][C:14]([C:16]3[CH:17]=[CH:18][C:19]([N:26]4[CH2:31][CH2:30][CH2:29][C@@H:28]([CH2:32][C:33]([O:35]C)=[O:34])[CH2:27]4)=[N:20][C:21]=3[S:22][CH2:23][CH2:24][CH3:25])=[O:15])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.Cl>O.CO.C1COCC1.CCOC(C)=O>[C:3]12([NH:13][C:14]([C:16]3[CH:17]=[CH:18][C:19]([N:26]4[CH2:31][CH2:30][CH2:29][C@@H:28]([CH2:32][C:33]([OH:35])=[O:34])[CH2:27]4)=[N:20][C:21]=3[S:22][CH2:23][CH2:24][CH3:25])=[O:15])[CH2:12][CH:7]3[CH2:6][CH:5]([CH2:11][CH:9]([CH2:8]3)[CH2:10]1)[CH2:4]2

Participants

Conditions

Temperature: 18 °C

Procedure

A solution of lithium hydroxide (0.053 g, 1.26 mmol) in water (1 mL) was added dropwise to a stirred solution of methyl {(3S)-1-[5-(adamantan-1-ylcarbamoyl)-6-(propylthio)pyridin-2-yl]piperidin-3-yl}acetate (Intermediate 73, 204 mg, 0.42 mmol) in MeOH (3 mL) and THF (2 mL) at 18° C., over a period of 1 minute. The resulting solution was stirred at 18° C. for 20 hours. The reaction mixture was adjusted to pH 4.5 with 2M HCl and the reaction mixture was diluted with EtOAc (50 mL), and washed sequentially with water (20 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford {(3S)-1-[5-(adamantan-1-ylcarbamoyl)-6-(propylthio)pyridin-2-yl]piperidin-3-yl}acetic acid (180 mg, 91%), as a white solid.

Workup

washwashed sequentially with water (20 mL) and saturated brine (20 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-441b865162e84f84b5957ebc9ba7bb2c
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673938B2

Reaction notes

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