Dimethylamine → (R)-N,N-Dimethyl-3-[(2-nitro-4-sulfamoylphenyl)amino]-4-phenylsulfanylbutanamide

HRID 2085698Notes

Reaction equation

HRID 2085698 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].[CH3:28][NH:29][CH3:30].CCN=C=NCCCN(C)C>C1COCC1.CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[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]([N:29]([CH3:30])[CH3:28])=[O:15])=[C:7]([N+:25]([O-:27])=[O:26])[CH:6]=1)(=[O:4])=[O:3]

Participants

8

Reactant 3

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11683013(r)-3-(2-Nitro-4-sulfamoylphenylamino)-4-(phenylthio)butanoic acid

Product 1

HCID 11553925(R)-N,N-Dimethyl-3-[(2-nitro-4-sulfamoylphenyl)amino]-4-phenylsulfanylbutanamide

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 122E (411 mg, 1 mmol), 2M dimethylamine in THF (1 mL), EDCI (296 mg, 1.5 mmol), and DMAP (10 mg) in DMF (10 mL) at room temperature was stirred for 16 hours, diluted with ethyl acetate (200 mL), washed sequentially with 1N HCl (50 mL), water (50 mL), and brine (20 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 100% ethyl acetate to provide the desired product. MS (ESI(+)) m/e 439 (M+H)+.

Workup

  1. washwashed sequentially with 1N HCl (50 mL), water (50 mL), and brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 100% ethyl acetate

Sources & evidence

ORD record
ord-6f406aba480445cba8daba0f4872de50
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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