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

HRID 392924Notes

Reaction equation

HRID 392924 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-ca3e10c13e70400e973ec73709bc66d7
Source dataset
uspto-grants-2004_10
Patent number
US06803484B2

Reaction notes

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