Hydrochloric Acid → (R)-4-((4-(Dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrobenzenesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Borane	HCID 6331	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	(R)-N,N-Dimethyl-3-[(2-nitro-4-sulfamoylphenyl)amino]-4-phenylsulfanylbutanamide	HCID 11553925	—
Solvent	Methanol	HCID 887	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(R)-4-((4-(Dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrobenzenesulfonamide	HCID 11502754	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of Example 122F (4.06 g, 9.25 mmol) and 1M borane in THF (20 mL) at room temperature was stirred for 16 hours, treated with methanol (5.0 mL) and concentrated HCl (2 mL), stirred at 80° C. for 3 hours, cooled to room temperature, adjusted to pH>7 with 4M sodium carbonate, diluted with ethyl acetate (150 mL), washed with water (50 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20% methanol/dichloromethane to provide the desired product. MS (ESI(+)) m/e 425 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07504512B2
Source dataset	uspto-grants-2009_03
ORD ID	ord-bb7de1db3db949feb09ea1166d34ec3f
Source note	uspto-grants-2009_03