Water → 2-Amino-5-butyryl-4-trifluoromethyl-benzoic acid methyl ester

HRID 1441550Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:10](=[O:14])[CH2:11][CH2:12][CH3:13])[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:5]=1[NH:19]C(=O)C.O.OS(O)(=O)=O>CO.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:10](=[O:14])[CH2:11][CH2:12][CH3:13])[C:7]([C:15]([F:17])([F:18])[F:16])=[CH:6][C:5]=1[NH2:19]

Participants

Conditions

Temperature: 60 °C

Procedure

2-Acetylamino-5-butyryl-4-trifluoromethyl-benzoic acid methyl ester (234 mg, 0.706 mmol) was dissolved in MeOH (2.4 mL). Water (500 uL) was added, followed by dropwise addition of concd H2SO4 (254 uL). The reaction mixture was heated to 60° C. for 1 h to give a light yellow suspension. The reaction mixture was diluted with EtOAc, poured onto water/EtOAc and the pH was adjusted to 8 with sat. aq KHCO3. The organic phase was washed with brine, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo. The obtained residue was purified by flash column chromatography (10 g silica gel, hexanes/EtOAc (1:0→7:3)) to afford the title compound (168 mg, 82%) as a colorless foam. ESI-MS: m/z 290 [M+H]+, m/z 288 [M−H]−.

Workup

customto give a light yellow suspension
additionpoured onto water/EtOAc
washThe organic phase was washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customThe obtained residue was purified by flash column chromatography (10 g silica gel, hexanes/EtOAc (1:0→7:3))

Sources & evidence

ORD record: ord-5353f8e5c8734df983ac8ab6fd56cccc
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655666B2

Reaction notes

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