Trifluoroacetic acid → HCID 67169171, compound

HRID 1506433Notes

Reaction equation

CC1(C)[O:6][CH:5]([C:7]2[CH:8]=[CH:9][C:10]3[C:16]4=[N:17][O:18][C:19]([C:20]5[O:24][N:23]=[C:22]([C:25]6[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=6)[C:21]=5[C:31]([F:34])([F:33])[F:32])=[C:15]4[CH2:14][O:13][C:11]=3[CH:12]=2)[CH2:4][O:3]1.C(O)(C(F)(F)F)=O>>[C:25]1([C:22]2[C:21]([C:31]([F:34])([F:33])[F:32])=[C:20]([C:19]3[O:18][N:17]=[C:16]4[C:10]5[CH:9]=[CH:8][C:7]([CH:5]([OH:6])[CH2:4][OH:3])=[CH:12][C:11]=5[O:13][CH2:14][C:15]=34)[O:24][N:23]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67171508HCID 67171508, compound

Product 1

HCID 67169171HCID 67169171, compoundYield 101.1%

Procedure

A solution of 7-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[4,3-c]isoxazole (Preparation 61B, 0.042 g, 0.087 mmol) in TFA (1.00 ml, 13.0 mmol) was left standing at room temperature for 45 min. The TFA was removed under reduced pressure, and the residue was diluted with dichloromethane, washed with a saturated aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded 1-(3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[4,3-c]isoxazol-7-yl)ethane-1,2-diol (0.039 g, 0.088 mmol, 100% yield) as an off-white solid. The product had an HPLC ret. time=3.00 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=444.9.

Workup

customThe TFA was removed under reduced pressure
additionthe residue was diluted with dichloromethane
washwashed with a saturated aqueous solution of sodium bicarbonate
dry with materialdried over anhydrous sodium sulfate
concentrationConcentration under reduced pressure

Sources & evidence

ORD record: ord-25029f853a82466e80a798d880a6b92d
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216972B2

Reaction notes

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