Hydrochloric Acid → 2-(R)-{[4-(5-chloropyridin-2-yloxy)piperidine-1-sulfonyl]amino}-3-methylbutyric acid

HRID 842998Notes

Reaction equation

O.[OH-].[Li+].[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH:12]2[CH2:17][CH2:16][N:15]([S:18]([NH:21][C@H:22]([CH:27]([CH3:29])[CH3:28])[C:23]([O:25]C)=[O:24])(=[O:20])=[O:19])[CH2:14][CH2:13]2)=[N:9][CH:10]=1.Cl>O.CO.O1CCCC1>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH:12]2[CH2:17][CH2:16][N:15]([S:18]([NH:21][C@H:22]([CH:27]([CH3:29])[CH3:28])[C:23]([OH:25])=[O:24])(=[O:20])=[O:19])[CH2:14][CH2:13]2)=[N:9][CH:10]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of lithium hydroxide monohydrate (0.35 g, 8.3 mmol) in water (5 ml) was added to a solution of methyl (R)-2-{[4-(5-chloropyridin-2-yloxy)piperidine-1 sulfonyl]amino}-3-methylbutyrate (1.7 g, 4.2 mmol), [prepared as described in Example 2], in methanol/tetrahydrofuran (1:1, 25 ml) and the reaction mixture was warmed to 45° C. After stirring overnight, reaction mixture was adjusted to pH 6 using 1M HCl and the product was extracted into ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed (SiO2, 2% methanol/methylene chloride) to give 2-(R)-{[4-(5-chloropyridin-2-yloxy)piperidine-1-sulfonyl]amino}-3-methylbutyric acid as a white gummy solid (66%).

Workup

customreaction mixture
extractionthe product was extracted into ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was chromatographed (SiO2, 2% methanol/methylene chloride)

Sources & evidence

ORD record: ord-2144d97a9aca4843b59641d22d718d9a
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376506B1

Reaction notes

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