Ethyl bromoacetate → Ethyl N-{4-chloro-2-[(2-chlorophenyl)(hydroxy)methyl]phenyl}-N-[(3,4-dimethoxyphenyl)sulfonyl]glycinate

HRID 747593Notes

Reaction equation

HRID 747593 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([CH:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[OH:23])[CH:3]=1.[H-].[Na+].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:10])=[O:11])[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:4]([CH:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[OH:23])[CH:3]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 68566152N-{4-chloro-2-[(2-chlorophenyl)(hydroxy)methyl]phenyl}-3,4-dimethoxybenzenesulfonamide

Product 1

HCID 11548525Ethyl N-{4-chloro-2-[(2-chlorophenyl)(hydroxy)methyl]phenyl}-N-[(3,4-dimethoxyphenyl)sulfonyl]glycinate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 6 g of N-{4-chloro-2-[(2-chlorophenyl)(hydroxy)methyl]phenyl}-3,4-dimethoxybenzenesulfonamide dissolved in 50 ml of DMF at 0° C. is added portionwise 0.674 g of sodium hydride. After 1 hour at 0° C., 1.4 ml of ethyl 2-bromoacetate are introduced and the mixture is left for 18 hours at room temperature. The reaction medium is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with dichloromethane to give 1.3 g of the expected product.

Workup

  1. waitthe mixture is left for 18 hours at room temperature
  2. washwashed with water
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a column of silica gel
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-a79cba145dbd4c0a979ae4cb3e65ebd5
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

Loading…