Sodium Thiosulfate → HCID 86646747, compound

HRID 888350Notes

Reaction equation

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

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-66879796fc144a838910645db2daeab2
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247401B2

Reaction notes

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