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

HRID 392924ノート

反応式

HRID 392924 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-ca3e10c13e70400e973ec73709bc66d7
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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