Triethylamine → HCID 86653047, 화합물

HRID 2060823노트

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HRID 2060823 반응식
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]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 67196247trans-N-(4-hydroxytetrahydrofuran-3-yl)propane-2-sulfonamide

생성물 1

HCID 86653047HCID 86653047, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d2ff0b7024294e11ba36d6c5ba36c6b5
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278457B2

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