Sodium Hydroxide → (R)-5-(sec-butylamino)-4-(aminocarbonyl)-2-methylbenzoic acid

HRID 906156Notes

Reaction equation

[C@H:1]([NH:5][C:6]1[C:7]([C:17]([NH2:19])=[O:18])=[CH:8][C:9]([CH3:16])=[C:10]([CH:15]=1)[C:11]([O:13]C)=[O:12])([CH2:3][CH3:4])[CH3:2].[OH-].[Na+]>CO.ClCCl>[C@H:1]([NH:5][C:6]1[C:7]([C:17]([NH2:19])=[O:18])=[CH:8][C:9]([CH3:16])=[C:10]([CH:15]=1)[C:11]([OH:13])=[O:12])([CH2:3][CH3:4])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of (R)-methyl 5-(sec-butylamino)-4-(aminocarbonyl)-2-methylbenzoate (300 mg, 1.13 mmol) in methanol (2.0 mL) and dichloromethane (1.0 mL) was added 2.0M aqueous sodium hydroxide solution (2.0 mL, 4.0 mmol). The reaction mixture was heated to 45° C. and stirred for 2 h, at which time it was cooled to room temperature and all volatiles were removed by rotary evaporation. To the residual solution was slowly added 1.0M aqueous hydrochloric acid until pH<2. The yellow precipitate was collected by filtration and washed with water to afford (R)-5-(sec-butylamino)-4-(aminocarbonyl)-2-methylbenzoic acid (210 mg, 65%). MS (EI) for C13H18N2O3: 251 (MH+).

Workup

temperaturewas cooled to room temperature
customall volatiles were removed by rotary evaporation
filtrationThe yellow precipitate was collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-dc1d41624d02438e970f5fb5ca2990d4
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012956B2

Reaction notes

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