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

HRID 392924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 392924
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ca3e10c13e70400e973ec73709bc66d7
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06803484B2

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