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

HRID 1720626Notes

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-9a0cb5fe3355418aae24e8b7f8573bdb
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05506242

Reaction notes

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