Dichloromethane → HCID 57748232, compound

HRID 906173Notes

Reaction equation

[NH2:1][C:2]([C:4]1[C:13]([NH:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([F:20])[CH:5]=1)=[O:3].[OH-].[Na+].ClCCl>CO>[NH2:1][C:2]([C:4]1[C:13]([NH:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([F:20])[CH:5]=1)=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 4-(aminocarbonyl)-2-fluoro-5-(pentan-3-ylamino)benzoate (73.7 mg, 0.26 mmol) in methanol (1 mL) at 0° C. was added 1 N sodium hydroxide (520 uL, 0.52 mmol). The mixture was stirred 30 min at 0° C., and was then warmed to room temperature. Dichloromethane (500 uL) was added to improve solubility, and the homogeneous solution was stirred 3.5 h at room temperature. After acidification with 1 N hydrochloric acid (500 uL), the volatile solvents were removed by rotary evaporation. An insoluble solid material was then isolated from the aqueous residue by filtration. The solid was dried to give 4-(aminocarbonyl)-2-fluoro-5-(pentan-3-ylamino)benzoic acid (61.7 mg, 0.23 mmol, 88% yield). 1H NMR (400 MHz, CD3OD): 7.41 (d, 1H), 7.16 (d, 1H), 3.43-3.28 (m, 1H buried), 1.68-1.46 (m, 4H), 0.95 (t, 6H).

Workup

temperaturewas then warmed to room temperature
stirringthe homogeneous solution was stirred 3.5 h at room temperature
customAfter acidification with 1 N hydrochloric acid (500 uL), the volatile solvents were removed by rotary evaporation
customAn insoluble solid material was then isolated from the aqueous residue by filtration
customThe solid was dried

Sources & evidence

ORD record: ord-b619a67dce414d5ebc0b6c64ec934740
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012956B2

Reaction notes

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