Potassium Carbonate → (R)-2-(1-aminopropyl)-N-tert-butylbenzenesulfonamide

HRID 42346Notes

Reaction equation

HRID 42346 reaction equation
FC(F)(F)C([NH:5][C@@H:6]([C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])=[O:16])=[CH:11][CH:10]=1)[CH2:7][CH3:8])=O.FC(F)(F)C([NH:29][C@@H:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[S:39]([NH:42][C:43]([CH3:46])([CH3:45])[CH3:44])(=[O:41])=[O:40])[CH2:31][CH3:32])=O.C([O-])([O-])=O.[K+].[K+]>CO.O>[NH2:5][C@@H:6]([C:9]1[CH:10]=[CH:11][C:12]([S:15]([NH:18][C:19]([CH3:20])([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:13][CH:14]=1)[CH2:7][CH3:8].[NH2:29][C@@H:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[S:39]([NH:42][C:43]([CH3:44])([CH3:46])[CH3:45])(=[O:41])=[O:40])[CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 58275441(R)-4-(1-(2,2,2-trifluoroacetamido)propyl)-N-tert-butyl-benzenesulfonamideHCID 86653619(R)-2-(1-(2,2,2-trifluoroacetamido)propyl)-N-tert-butyl-benzenesulfonamide

Product 2

HCID 58275405(R)-2-(1-aminopropyl)-N-tert-butylbenzenesulfonamideHCID 58275434(R)-4-(1-aminopropyl)-N-tert-butylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of (R)-4-(1-(2,2,2-trifluoroacetamido)propyl)-N-tert-butyl-benzenesulfonamide and (R)-2-(1-(2,2,2-trifluoroacetamido)propyl)-N-tert-butyl-benzenesulfonamide (0.501 g), K2CO3 (0.947 g) in MeOH/H2O (1:1, 20 ml) was stirred at room temperature overnight and then heated at 60° C. for 3 hours. The reaction mixture was cooled to room temperature and concentrated to about 3 ml. The residue was acidified with TFA to ca. pH 1. The solution was co-evaporated with acetonitrile (2×) and then purified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA) to give 0.2033 g (R)-4-(1-aminopropyl)-N-tert-butylbenzenesulfonamide as white powder after lyophilization and 63.4 mg (R)-2-(1-aminopropyl)-N-tert-butylbenzenesulfonamide as a white powder after lyophilization.

Workup

  1. temperatureheated at 60° C. for 3 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated to about 3 ml
  4. custompurified by reverse phase HPLC (5-100% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-ec269aa0cbb8425abc1d1af8ea491b3f
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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