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

HRID 1798845Notes

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-dadffe2f642f47939d1da51bdf712ab3
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343987B2

Reaction notes

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