Triethylamine → HCID 86653047、化合物

HRID 2060823ノート

反応式

HRID 2060823 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 86653047HCID 86653047、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d2ff0b7024294e11ba36d6c5ba36c6b5
出典データセット
uspto-grants-2012_10
特許番号
US08278457B2

反応ノート

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