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

HRID 2209716Notes

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-f37e5abb12aa44138d327e6730f9d888
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455258

Reaction notes

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