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

HRID 392930노트

반응식

HRID 392930 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-54d1aeef72c2498d8b3d39e0faea7f27
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803484B2

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