Sodium Thiosulfate → HCID 86646747, compound

HRID 1047594Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([C:10]1[CH:11]=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].C(C1C=C(C)C=C(C(C)(C)C)C=1[OH:36])(C)(C)C.ClC1C=CC=C(C(OO)=O)C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([C:10]1[CH:11]=[N+:12]([O-:36])[C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=1)[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of tert-butyl{(1R)-1-[6-(trifluoromethyl)-3-pyridinyl]ethyl}carbamate (0.626 g, 2.157 mmol) in chloroform (10.0 mL) were added 2,6-di-tert-butyl-4-methylphenol (24 mg, 0.108 mmol) and 3-chloroperbenzoic acid (0.665 g, 2.70 mmol). The reaction mixture was stirred at 50° C. for 48 h. The reaction mixture was cooled to ambient temperature. Saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate were added. The mixture was extracted with dichloromethane (3×). The combined organics extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (75% hexanes/ethyl acetate→100% ethyl acetate) gave the title compound (140 mg). MS 307.0 (M+1).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
extractionThe mixture was extracted with dichloromethane (3×)
washThe combined organics extracts were washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customPurification by silica gel chromatography (75% hexanes/ethyl acetate→100% ethyl acetate)

Sources & evidence

ORD record: ord-b43487f7d2fb433e8988b23b79309fa4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569512B2

Reaction notes

Loading…