Triethylamine → N-((1R)-1-Benzyl-2-((methylsulfonyl)amino)ethyl)-N-methylcarbamic acid tert-butylester

HRID 1601997Notes

Reaction equation

[C:1]([O:5][C:6](=[O:19])[N:7]([C@@H:9]([CH2:17][NH2:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:17][NH:18][S:28]([CH3:27])(=[O:30])=[O:29])[CH3:8])([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

N-((1R)-1-Aminomethyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester (830 mg, 3.14 mmol) was dissolved in dichloromethane (15 ml). Triethylamine (0.44 ml, 3.14 mmol) was added. The solution was cooled to -78° C. A solution of methanesulfonyl chloride (0.24 ml, 3.14 mmol) in dichloromethane (2 ml) was added dropwise. The reaction mixture was stirred for 16 h, while it was warming up to room temperature. It was diluted with dichloromethane (100 ml) and washed with saturated sodium chloride solution (100 ml). It was dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (65 g), using ethyl acetate/heptane (2:1) as eluent, to give 990 mg of N-((1R)-1-Benzyl-2-((methylsulfonyl)amino)ethyl)-N-methylcarbamic acid tert-butylester.

Workup

temperaturewas warming up to room temperature
washwashed with saturated sodium chloride solution (100 ml)
dry with materialIt was dried over magnesium sulfate
customThe solvent was removed in vacuo
customThe crude product was purified by flash chromatography on silica (65 g)

Sources & evidence

ORD record: ord-568efab1994a4a759a95602ec1da4677
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977178

Reaction notes

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