Water → tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate

HRID 1366250Notes

Reaction equation

[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>ClCCl>[CH3:19][S:20]([O:1][CH2:2][CH2:3][NH:4][C:5]([O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:11])(=[O:22])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

1 g (6.2 mmol) tert.-butyl (2-hydroxyethyl)carbamate and 0.75 g (7.44 mmol) triethylamine are dissolved in 250 ml dichloromethane and the solution is cooled to 0° C. 0.78 g (6.82 mmol) methanesulfonyl chloride are added slowly. The reaction mixture is stirred at 0° C. for one hour, then water is added, and the aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate, evaporated to dryness in vacuo, and the crude product is purified by column chromatography (silica, eluent: cyclohexane/ethyl acetate 5:1→2:1).

Workup

extractionthe aqueous phase is extracted three times with ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulfate
customevaporated to dryness in vacuo
customthe crude product is purified by column chromatography (silica, eluent: cyclohexane/ethyl acetate 5:1→2:1)

Sources & evidence

ORD record: ord-e9a838452ff54f43944bc2dc0ff2a8c7
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893073B2

Reaction notes

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