Methanol → HCID 57974070, compound

HRID 1866617Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:14][S:13][CH2:12][C:11](=[O:15])[N:10]2[CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH:5]=[C:6]([F:8])[CH:7]=1.C[OH:28]>OO.Cl>[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:14][S:13](=[O:28])[CH2:12][C:11](=[O:15])[N:10]2[CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of benzyl [(3R)-3-(3,5-difluorophenyl)-5-oxothiomorpholin-4-yl]acetate (151 mg, 0.399 mmol, from Step A.) in MeOH (10 mL) was added aqueous hydrogen peroxide (30 drops, ˜0.8 mL, 30% by weight), and aqueous HCl (5 drops, 3 M HCl). This mixture was then heated to 40° C. for 2.5 hours. After cooling to ambient temperature, the bulk of the MeOH was removed in vacuo, and the residue was partitioned between 50 mL of water and 100 mL of diethyl ether. The organics were washed with saturated brine, then dried over sodium sulfate, filtered, and concentrated in vacuo to give a residue that was purified by silica gel chromatography eluting with a gradient of Hexanes:EtOAc—1:1 to 100% EtOAc, to yield 24.5 mg of the minor sulfoxide isomer and 93.6 mg of the major sulfoxide isomer. MS: m/z=394 (M+1).

Workup

temperatureAfter cooling to ambient temperature
customthe bulk of the MeOH was removed in vacuo
customthe residue was partitioned between 50 mL of water and 100 mL of diethyl ether
washThe organics were washed with saturated brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto give a residue that
customwas purified by silica gel chromatography
washeluting with a gradient of Hexanes

Sources & evidence

ORD record: ord-c63c25c8002a4022a7f900ff23cd3fdf
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629338B2

Reaction notes

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