Water → HCID 53638526, compound

HRID 1268645Notes

Reaction equation

C(O[C:6](=O)[N:7](C)[C@H:8]([CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[CH2:9][N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].O>ClCCl>[CH3:15][N:10]([CH2:9][C@H:8]([NH:7][CH3:6])[CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[S:11]([CH3:14])(=[O:13])=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of of N-methyl-N-((1R)-2-(N-methyl-N-(methylsulfonyl)amino)-1-((2-thienyl)methyl)ethyl)carbamic acid tert-butyl ester (1.87 g, 7.12 mmol) in dichloromethane (7 ml) was cooled to 0° C. Trifluoroacetic acid (7 ml) was added. The reaction mixture was stirred for 45 min at 0° C. Dichloromethane (10 ml) was added. A saturated aqueous solution of sodium hydrogen carbonate (10 ml) was added. Solid sodium hydrogen carbonate was added until pH 7.Water (100 ml) was added, until a clear solution was obtained. The phases were separated. The aqueous phase was extracted with dichloromethane (2×50 ml). The combined organic phases were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (120 g), using dichloromethane/methanol/25% aqueous ammonia as eluent, to give 1.24 g of N-methyl-N-((2R)-2-(methylamino)-3-(2-thienyl)propyl)methanesulfonamide.

Workup

customwas obtained
customThe phases were separated
extractionThe aqueous phase was extracted with dichloromethane (2×50 ml)
dry with materialThe combined organic phases were dried over magnesium sulfate
customThe solvent was removed in vacuo
customThe crude product was purified by flash chromatography on silica (120 g)

Sources & evidence

ORD record: ord-8bc9225ec3f7453792a079e22570f637
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555570B2

Reaction notes

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