m-Chloroperbenzoic acid → Tert-butyl 4-{5-bromo-4-[4-(methylsulfinyl)phenyl]-1,3-oxazol-2-yl}piperidine-1-carboxylate

HRID 716711Notes

Reaction equation

[Br:1][C:2]1[O:6][C:5]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[N:4][C:3]=1[C:20]1[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=1.ClC1C=C(C=CC=1)C(OO)=[O:33]>C(Cl)Cl>[Br:1][C:2]1[O:6][C:5]([CH:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)=[N:4][C:3]=1[C:20]1[CH:21]=[CH:22][C:23]([S:26]([CH3:27])=[O:33])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 25 °C

Procedure

tert-Butyl 4-{5-bromo-4-[4-(methylsulfanyl)phenyl]-1,3-oxazol-2-yl}piperidine-1-carboxylate (705 mg, 1.55 mmol) was dissolved in methylene chloride (15.5 nit) under argon atmosphere. 3-Chloroperoxybenzoic acid (383 mg, 1.55 mL) was dissolved in methylene chloride (3.1 mL) and added via syringe to the stirring solution. The resulting solution was stirred at 25° C. for 1 hour. The solution was then diluted with methylene chloride (15 mL) and washed with saturated sodium bicarbonate followed by brine. The organics were dried over sodium sulfate and concentrated in vacuo to yield 680 mg of the desired product as colorless oil. LCMS (M+1)=469.40

Workup

additionadded via syringe to the stirring solution
washwashed with saturated sodium bicarbonate
dry with materialThe organics were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ab9715020746402f92dfe10fba0efcc5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193697B2

Reaction notes

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