Trifluoroacetic acid → HCID 68277965, compound

HRID 931523Notes

Reaction equation

C([O:5][C:6](=[O:32])[CH:7]([C:25]([O:27]C(C)(C)C)=[O:26])[CH2:8][C:9]1[N:10]=[C:11]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)[O:12][C:13]=1[CH3:14])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:22][O:21][C:19]([C:18]1[CH:23]=[CH:24][C:15]([C:11]2[O:12][C:13]([CH3:14])=[C:9]([CH2:8][CH:7]([C:6]([OH:32])=[O:5])[C:25]([OH:27])=[O:26])[N:10]=2)=[CH:16][CH:17]=1)=[O:20]

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of methyl 4-(4-(3-tert-butoxy-2-(tert-butoxycarbonyl)-3-oxopropyl)-5-methyloxazol-2-yl)benzoate (4.0 g, 8.99 mmol, 1.00 equiv) in dichloromethane (20 mL) was added trifluoroacetic acid (20 mL). The reaction mixture was stirred overnight at 35° C. and then concentrated under vacuum to remove dichloromethane. Saturated sodium bicarbonate solution was added to the residue until the pH value of the solution was adjusted to 2-3. The resulting solution was extracted with 200 mL of ethyl acetate. The organic layer was washed with 2×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to yield 3.0 g (100%) of 2-((2-(4-(methoxycarbonyl)phenyl)-5-methyloxazol-4-yl)methyl)malonic acid as a light yellow solid. LC-MS: (ES, m/z): 334 [M+H]+, 272, 115.

Workup

concentrationconcentrated under vacuum
customto remove dichloromethane
additionSaturated sodium bicarbonate solution was added to the residue until the pH value of the solution
extractionThe resulting solution was extracted with 200 mL of ethyl acetate
washThe organic layer was washed with 2×50 mL of brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-63ec081c3d3f40fcb99facfa1a49305a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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