p-Toluenesulfonic acid → HCID 86687901, compound

HRID 869006Notes

Reaction equation

O[C:2]1([C:20]([F:23])([F:22])[F:21])[CH2:7][C:6](O)([C:8]([F:11])([F:10])[F:9])[NH:5][C:4]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[F:11][C:8]([F:9])([F:10])[C:6]1[CH:7]=[C:2]([C:20]([F:23])([F:21])[F:22])[N:3]=[C:4]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:5]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of ethyl 3-(4,6-dihydroxy-4,6-bis(trifluoromethyl)-1,4,5,6-tetrahydropyrimidin-2-yl)propanoate (400 mg, 1.14 mmol), p-toluenesulfonic acid (210 mg, 1.14 mmol), and toluene was heated to 110° C. for 2 h. The reaction was then cooled to room temperature, the mixture was neutralized with saturated sodium carbonate solution to pH 7 and then extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine (30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure; and the residue was purified by prep-TLC to give the title compound (100 mg). MS (ESI): m/z 317 [M+H]+

Workup

temperatureThe reaction was then cooled to room temperature
extractionextracted with EtOAc (50 mL×3)
washThe combined organic layers were washed with brine (30 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customand the residue was purified by prep-TLC

Sources & evidence

ORD record: ord-49477fdc25a74c14a80c07834318f024
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969349B2

Reaction notes

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