Hydrochloric Acid → 4-(((1r)-3-Hydroxy-1-((phenylthio)methyl)propyl)amino)-3-nitrobenzenesulfonamide

HRID 1785821Notes

Reaction equation

HRID 1785821 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C@@H:12]([CH2:17][S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][C:14](O)=[O:15])=[C:7]([N+:25]([O-:27])=[O:26])[CH:6]=1)(=[O:4])=[O:3].B.CO.Cl>C1COCC1.C(OCC)(=O)C>[OH:15][CH2:14][CH2:13][C@@H:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([NH2:1])(=[O:4])=[O:3])=[CH:6][C:7]=1[N+:25]([O-:27])=[O:26])[CH2:17][S:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 11683013(r)-3-(2-Nitro-4-sulfamoylphenylamino)-4-(phenylthio)butanoic acid

Product 1

HCID 684535934-(((1r)-3-Hydroxy-1-((phenylthio)methyl)propyl)amino)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 122E (206 mg, 0.50 mmol) and 1M borane in THF (20 mL) was stirred for 16 hours, treated sequentially with methanol (5.0 mL) and 1N HCl (2.0 mL), diluted with ethyl acetate (50 mL), washed with water (2 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/dichloromethane to provide the desired product. MS (ESI(+)) m/e 398 (M+H)+.

Workup

  1. washwashed with water (2 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-a67cc521a5ee4cbb948d924c7a59089c
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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