Triethylamine → HCID 86653047, compound

HRID 2360318Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (1.99 mL, 14.3 mmol) was added to a cooled (0° C.) solution of trans-N-(4-hydroxytetrahydrofuran-3-yl)propane-2-sulfonamide (1.99 g, 9.52 mmol) in dichloromethane (20 mL). Methanesulfonyl chloride (0.885 mL, 11.4 mmol) was then added and the reaction was stirred at 0° C. for 50 minutes. Saturated aqueous sodium bicarbonate solution (10 mL) was added, and the aqueous layer was extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, concentrated in vacuo and purified by silica gel chromatography (Gradient: 10% to 50% ethyl acetate in heptane) to provide trans-4-[(isopropylsulfonyl)amino]tetrahydrofuran-3-yl methanesulfonate. Yield: 2.27 g, 7.90 mmol, 83%. 1H NMR (400 MHz, CDCl3) δ 1.40 (d, J=6.8 Hz, 3H), 1.41 (d, J=6.8 Hz, 3H), 3.14 (s, 3H), 3.25 (septet, J=6.8 Hz, 1H), 3.77 (dd, J=9.5, 2.4 Hz, 1H), 3.96 (dd, J=11.3, 2.2 Hz, 1H), 4.08-4.16 (m, 2H), 4.21 (dd, J=11.3, 5.1 Hz, 1H), 4.77 (d, J=8.0 Hz, 1H), 5.15 (m, 1H). 13C NMR (100 MHz, CDCl3) δ 16.48, 16.54, 38.28, 54.28, 59.49, 71.83, 71.87, 83.97.

Workup

extractionthe aqueous layer was extracted with methylene chloride
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (Gradient: 10% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-41b3a41f1b6e4d5c9b8001feacde8db4
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686043B2

Reaction notes

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