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

HRID 2356033Notes

Reaction equation

[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C@@H:12]([CH2:19][S:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=O)=[C:7]([N+:27]([O-:29])=[O:28])[CH:6]=1)(=[O:4])=[O:3].B.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.CO>[CH3:18][N:16]([CH3:17])[CH2:14][CH2:13][C@@H:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([NH2:1])(=[O:3])=[O:4])=[CH:6][C:7]=1[N+:27]([O-:29])=[O:28])[CH2:19][S:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

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)+.

Workup

temperaturecooled to room temperature
washwashed with water (50 mL) and brine (10 mL)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe concentrate was purified by flash column chromatography on silica gel with 20% methanol/dichloromethane

Sources & evidence

ORD record: ord-d23868c629f84ebfb8ffbd627575cf24
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754886B2

Reaction notes

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