Dichloromethane → 2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methyl-butanoic acid hydrochloride

HRID 264280Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[C@H:13]([CH:21]([CH3:23])[CH3:22])[C:14]([O:16]C(C)(C)C)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)[Cl:32]>>[ClH:32].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[C@H:13]([CH:21]([CH3:23])[CH3:22])[C:14]([OH:16])=[O:15])(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 6344Dichloromethane

HCID 11797104t-Butyl 2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanoate

Product 1

HCID 700617032(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methyl-butanoic acid hydrochloride

Conditions

Temperature: -10 °C

Procedure

t-Butyl 2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanoate (5.3 g, 12.2 mmol) is dissolved in methylene chloride (150 mL) and cooled to -10° C. Hydrochloric acid gas is bubbled into the solution for 10 minutes. The reaction mixture is then sealed, warmed to room temperature and stirred for 4 hours. The solvent is then evaporated to provide 2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methyl-butanoic acid hydrochloride.

Workup

customHydrochloric acid gas is bubbled into the solution for 10 minutes
customThe reaction mixture is then sealed
temperaturewarmed to room temperature
customThe solvent is then evaporated

Sources & evidence

ORD record: ord-a3aff89067704164b900ff25c9c5c473
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646167

Reaction notes

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