Triethylamine → 2-{[(2-Nitrophenyl)sulfonyl]amino}ethyl methanesulfonate

HRID 514770Notes

Reaction equation

C(N(CC)CC)C.[OH:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13].[S:24](Cl)([CH3:27])(=[O:26])=[O:25].CCCCCC.C(OCC)(=O)C>C(OCC)(=O)C>[CH3:27][S:24]([O:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])(=[O:26])=[O:25]

Participants

Conditions

Temperature: 10 °C

Procedure

Triethylamine (20 mL, 144.6 mmol) was added to a solution of compound 54 (29.5 g, 119.9 mmol) in ethyl acetate (300 mL). The mixture was cooled to 10° C. in an ice bath. Then, a solution of mesyl chloride (10.2 mL, 131.8 mmol) in ethyl acetate (50 mL) was added dropwise at a temperature ≦20° C. The resulting solution was stirred at room temperature for 3 h (TLC monitoring, eluent: hexane-ethyl acetate, 4:1). The reaction mixture was filtered to remove the precipitate-triethylamine hydrochloride. The filtrate was washed with aqueous NaHCO3, water, and evaporated. Yield of 55: 32.2 g (83%) as crystals.

Workup

filtrationThe reaction mixture was filtered
customto remove the precipitate-triethylamine hydrochloride
washThe filtrate was washed with aqueous NaHCO3, water
customevaporated

Sources & evidence

ORD record: ord-612a917d996b4eb1b1be5063b1d96cbf
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108916B2

Reaction notes

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