Boron trifluoride etherate → 5-[4-(3-Methoxy-pyridin-2-yl)-oxazol-2-yl]-pentanoic acid methyl ester

HRID 551761Notes

Reaction equation

B(F)(F)F.CCOCC.Br[CH2:11][C:12]([C:14]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][N:15]=1)=O.[CH3:22][O:23][C:24](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][C:29](=[O:31])[NH2:30]>C1COCC1>[CH3:22][O:23][C:24](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[O:31][CH:11]=[C:12]([C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][N:15]=2)[N:30]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Add boron trifluoride etherate (0.30 mL, 1.00 mmol) to a sealed tube containing 2-bromo-1-(3-methoxy-pyridin-2-yl)-ethanone (231 mg, 1.00 mmol), 5-carbamoyl-pentanoic acid methyl ester (222 mg, 1.39 mmol), and THF (anhydrous, 3 mL). Flush with N2, seal, heat at 80° C. overnight. Partition between saturated aqueous NaHCO3 solution and 20% i-PrOH/CHCl3, separate layers. Extract from aqueous layer with 20% i-PrOH/CHCl3 (×3), dry combined organic layers with MgSO4 and concentrate. Adsorb on SiO2 and purify by flash chromatography on silica gel eluting with 1-3% methanol/CHCl3 to afford the title compound (97 mg, 33%). MS (IS) 291 (M+1)+.

Workup

customFlush with N2
customseal
customPartition between saturated aqueous NaHCO3 solution and 20% i-PrOH/CHCl3
customseparate layers
extractionExtract from aqueous layer with 20% i-PrOH/CHCl3 (×3)
dry with materialdry combined organic layers with MgSO4
concentrationconcentrate
custompurify by flash chromatography on silica gel eluting with 1-3% methanol/CHCl3

Sources & evidence

ORD record: ord-f6186240b7fe43fabefd6f0007fda820
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947841B2

Reaction notes

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