p-Toluenesulfonic acid monohydrate → 2-Amino-5-(1-isopropoxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester

HRID 906513Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH:10]([OH:12])[CH3:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17]C(=O)C.O.[C:23]1(C)[CH:28]=CC(S(O)(=O)=O)=C[CH:24]=1>CC(O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH:10]([O:12][CH:23]([CH3:28])[CH3:24])[CH3:11])[C:7]([C:13]([F:14])([F:15])[F:16])=[CH:6][C:5]=1[NH2:17]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-acetylamino-5-(1-hydroxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester (500 mg, 1.64 mmol) in i-PrOH (5 mL) was treated by addition of p-toluenesulfonic acid monohydrate (99.9 mg, 0.517 mmol) and stirred at 80° C. for 18 h. The reaction mixture was cooled then concentrated in vacuo. The residue was purified by column chromatography (silica gel, 5:1 hexanes/EtOAc) to give title product (69 mg, 14% yield) as colorless crystals. m.p.: 87-90° C., API-ES: m/z 306 [M+H]+.

Workup

temperatureThe reaction mixture was cooled
concentrationthen concentrated in vacuo
customThe residue was purified by column chromatography (silica gel, 5:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-411c468529cd41aba50f9f40664f3c53
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012988B2

Reaction notes

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