m-Chloroperbenzoic acid → tert-Butyl(4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-[4-(methylsulfinyl)phenyl]-1,3-oxazolidine-3-carboxylate

HRID 901075Notes

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17]([N:19]1[C@H:23]([CH2:24][F:25])[C@@H:22]([C:26]2[CH:31]=[CH:30][C:29]([S:32][CH3:33])=[CH:28][CH:27]=2)[O:21][C:20]1([CH3:35])[CH3:34])=[O:18])([CH3:15])([CH3:14])[CH3:13].C(=O)(O)[O-].[Na+]>ClCCl>[F:25][CH2:24][C@@H:23]1[C@@H:22]([C:26]2[CH:27]=[CH:28][C:29]([S:32]([CH3:33])=[O:9])=[CH:30][CH:31]=2)[O:21][C:20]([CH3:35])([CH3:34])[N:19]1[C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of m-chloroperbenzoic acid (14.3 g, 1.2 eq ) in 100 ml of dichloromethane was added drop wise to the solution of 13 (17.3 g) in 150 ml of dichloromethane at −20° C. The temperature was maintained at −20° C. for an additional 40 minutes. A saturated solution of sodium bicarbonate (80 ml) was added and stirred for 30 minutes. The organic layer was separated and washed with brine (50 ml) and dried over sodium sulfate. After purification (via a column) 13.4 g of the desired product (as a heavy oil) was obtained.

Workup

customThe organic layer was separated
washwashed with brine (50 ml)
dry with materialdried over sodium sulfate
customAfter purification (via a column) 13.4 g of the desired product (as a heavy oil)
customwas obtained

Sources & evidence

ORD record: ord-986206c2cdd34839b2ada8226bd85333
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361689B2

Reaction notes

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