Triethylamine → (R)-N-(2-(4-nitrophenyl)propyl)propane-2-sulfonamide

HRID 392930ノート

反応式

HRID 392930 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([CH3:13])[CH2:11][NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH:21]([S:24](Cl)(=[O:26])=[O:25])([CH3:23])[CH3:22]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]([CH3:13])[CH2:11][NH:12][S:24]([CH:21]([CH3:23])[CH3:22])(=[O:26])=[O:25])=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 51434705(2R)-2-(4-nitrophenyl)propan-1-amine

生成物 1

HCID 9965675(R)-N-(2-(4-nitrophenyl)propyl)propane-2-sulfonamide収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A 500 mL three necked round bottom flask equipped with a mechanical stirrer, thermometer and an addition funnel is charged with (2R)-2-(4-nitrophenyl)propylamine (11.75 g, 65.21 mmol), methylene chloride (150.0 mL) and triethylamine (18.2 mL, 130.4 mmol). To this solution at 0° C. was added isopropylsulfonyl chloride (8.92 mL, 63.9 mmol) over a period of 20 minutes. Reaction was then stirred to room temperature overnight, then quenched with 1N HCl (150.0 mL). The lower organic layer is separated and dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford [(2R)-2-(4-nitrophenyl)propyl][(methylethyl)sulfonyl]amine (14.11 g, 97%) as an oil; 1H nmr (CDCl3, 300 MHz) δ 1.26 (d, 3H, J=6.7 Hz), 1.31 (d, 6H), 3.06 (m, 1H), 3.30 (m, 1H), 4.25 (broad triplet, 1H), 7.38 (d, 2H), 8.10 (2H); 13C nmr (CDCl3, 300 MHz) δ 16.75, 18.95, 41.29, 50.15, 53.85, 124.22, 128.52, 151.26.

後処理

  1. customReaction
  2. customquenched with 1N HCl (150.0 mL)
  3. customThe lower organic layer is separated
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-54d1aeef72c2498d8b3d39e0faea7f27
出典データセット
uspto-grants-2004_10
特許番号
US06803484B2

反応ノート

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