Morpholine → (R)-4-(4-morpholino-4-oxo-1-(phenylthio)butan-2-ylamino)-3-nitrobenzenesulfonamide

HRID 333877Notes

Reaction equation

HRID 333877 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([S:10](=[O:13])(=[O:12])[NH2:11])[CH:7]=[CH:6][C:5]=1[NH:14][C@@H:15]([CH2:20][S:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:16][C:17](O)=[O:18])([O-:3])=[O:2].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[O:31]1[CH2:32][CH2:33][N:28]([C:17](=[O:18])[CH2:16][C@@H:15]([NH:14][C:5]2[CH:6]=[CH:7][C:8]([S:10]([NH2:11])(=[O:12])=[O:13])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:20][S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:29][CH2:30]1

Participants

7

Reactant 3

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11683013(r)-3-(2-Nitro-4-sulfamoylphenylamino)-4-(phenylthio)butanoic acid

Product 1

HCID 11591105(R)-4-(4-morpholino-4-oxo-1-(phenylthio)butan-2-ylamino)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 3

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

Procedure

To a mixture of Example 10D (0.75 g) and morpholine (0.318 g) in N,N-dimethylformamide (5 mL) were added N,N-dimethylpyridin-4-amine (0.445 g) and 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (0.699 g). The mixture was stirred overnight, diluted with ethyl acetate and washed with 5% aqueous HCl and water. The organic layer was dried over Na2SO4 and concentrated to give the title compound.

Workup

  1. washwashed with 5% aqueous HCl and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-87dc64b5f3234d6ab9c7417ce182d183
Source dataset
uspto-grants-2014_11
Patent number
US08883784B2

Reaction notes

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