Sulfuric Acid → 2-Amino-5-propionyl-4-trifluoromethyl-benzoic acid methyl ester

HRID 906518Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([C:10](=[O:13])[CH2:11][CH3:12])[C:7]([C:14]([F:17])([F:16])[F:15])=[CH:6][C:5]=1[NH:18]C(=O)C.S(=O)(=O)(O)O>CO.O.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([C:10](=[O:13])[CH2:11][CH3:12])[C:7]([C:14]([F:16])([F:15])[F:17])=[CH:6][C:5]=1[NH2:18]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-acetylamino-5-propionyl-4-trifluoromethyl-benzoic acid methyl ester (260 mg, 0.82 mmol) in MeOH (2.6 mL) and water (0.54 mL) was treated with concentrated sulfuric acid (0.26 mL) and the mixture was heated to 60° C. for 1 h. It was then allowed to cool to r.t., and diluted with EtOAc. This mixture was washed once with aqueous sodium hydrogencarbonate (pH=8), once with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel 60, hexanes/EtOAc 100:0→80:20) to furnish 2-amino-5-propionyl-4-trifluoromethyl-benzoic acid methyl ester (185 mg, 0.67 mmol, 82%) as a white powder, m.p. 141-144° C., ESI-MS: m/z 276 [M+H]+.

Workup

temperatureto cool to r.t.
washThis mixture was washed once with aqueous sodium hydrogencarbonate (pH=8), once with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography (silica gel 60, hexanes/EtOAc 100:0→80:20)

Sources & evidence

ORD record: ord-ee4ba6c29c0a4b47afcd536ae7ccf541
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012988B2

Reaction notes

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