Sodium Bicarbonate → [(2R)-2-(4-aminophenyl)propyl][(methylethyl)sulfonyl]amine

HRID 392924노트

반응식

HRID 392924 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]([CH3:28])[CH2:20][NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([C@@H:19]([CH3:28])[CH2:20][NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:17][CH:18]=1

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 21307342(R)-N-(2-(4-Aminophenyl)propyl)propane-2-sulfonamide 4-methylbenzenesulfonate

생성물 1

HCID 11379852[(2R)-2-(4-aminophenyl)propyl][(methylethyl)sulfonyl]amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of [(2R)-2-(4-aminophenyl)propyl][(methylethyl)sulfonyl]amine p-toluenesulfonate (41.2 g, 0.0961 mol) in CH2Cl2 (300 mL) was added saturated aqueous NaHCO3 until the pH of the aqueous phase was 6.5. The phases were separated and the organic phase was washed with 5% NaHCO3 (2×100 mL), H2O (100 mL), and concentrated to provide [(2R)-2-(4-aminophenyl)propyl][(methylethyl)sulfonyl]amine as an oil. After diluting the oil with diethyl ether (50 mL), crystallization began after 10 min. Caution: Heat of crystallization caused ether to boil. After the exotherm subsided (45 minutes), the suspension was filtered, and the filter cake was washed with diethyl ether (2×20 mL), and dried under reduced pressure to afford [(2R)-2-(4-aminophenyl)propyl][(methylethyl)sulfonyl]amine (21.7 g, 88.1%). 1H NMR (CDCl3, 300 MHz) δ7.00 (d, 2H, J=8.1); 6.66 (d, 2H, J=8.4), 3.83 (m, 1H), 3.65(br s, 2H), 3.31 (m, 1H), 3.09 (m, 2H), 2.85 (m, 1H), 1.30 (d, 3H, J=7.2), 1.26 (d, 3H, J=6.9), 1.24 (d, 3H, J=6.9).

후처리

  1. customThe phases were separated
  2. washthe organic phase was washed with 5% NaHCO3 (2×100 mL), H2O (100 mL)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ca3e10c13e70400e973ec73709bc66d7
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803484B2

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