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

HRID 264331Notes

Reaction equation

[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[C@H:14]([CH:19]([CH3:21])[CH3:20])[C:15]([O:17]C)=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1.Cl.C>O>[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[C@H:14]([CH:19]([CH3:21])[CH3:20])[C:15]([OH:17])=[O:16])(=[O:11])=[O:12])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Methyl 2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanoate hydrochloride (7164 g, 16.7 mol) is added to a solution of water (27 L) and concentrated hydrochloric acid (9 L), and heated to 120° C. for 3 days. After cooling down to room temperature, charcoal (350 g) is added, stirring is continued for 45 minutes, the reaction is filtered, and the solvent is evaporated. The crude solid is re-dissolved in methanol (7.1 L) and ethyl acetate (73 L), and cooled to 3° C. for 2 hours. The precipitated product is collected by filtration to give 2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanoic acid hydrochloride.

Workup

temperatureAfter cooling down to room temperature
filtrationthe reaction is filtered
customthe solvent is evaporated
dissolutionThe crude solid is re-dissolved in methanol (7.1 L)
temperatureethyl acetate (73 L), and cooled to 3° C. for 2 hours
filtrationThe precipitated product is collected by filtration

Sources & evidence

ORD record: ord-c70488d5ae7f4cb79e0249a2fc5f67b7
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646167

Reaction notes

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