Perchloric Acid → HCID 70855541, compound

HRID 591026Notes

Reaction equation

[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][N:14]4[C:19]=3[CH:20]([OH:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1.Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+]>C(OC(C)(C)C)(=O)C>[C:5]([O:26][CH:20]([C:19]1[N:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][CH2:4][C:5]=2[CH:10]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:10])([CH3:6])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 2-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)imidazo[1,2-a]pyridin-3-yl]-2-hydroxyacetate (53 mg, 0.15 mmol) in tert-butyl acetate (4.6 mL) at −20° C. was added perchloric acid (0.6 mL). The mixture was stirred at 0° C. for 2 hours before being poured into a saturated aqueous solution of sodium bicarbonate (10 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×10 mL). The organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 60/40) to provide the desired product (19d) (38 mg, 0.093 mmol, 57%) as a colorless oil.

Workup

customThe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate (2×10 mL)
dry with materialThe organic layers were dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 60/40)

Sources & evidence

ORD record: ord-fee40071ce6744f7aead51a7744b6158
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238026B2

Reaction notes

Loading…