2-Bromoacetamide → N2-{4-chloro-2-[hydroxy(3-methoxyphenyl)methyl]phenyl}-N2-[(3,4-dimethoxyphenyl)sulfonyl]glycinamide

HRID 747601Notes

Reaction equation

HRID 747601 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]=[C:26]([O:30][CH3:31])[CH:25]=2)[OH:23])[CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:39][C:40]([NH2:42])=[O:41]>C1COCC1>[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:11])=[O:10])[CH2:39][C:40]([NH2:42])=[O:41])=[C:4]([CH:22]([OH:23])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 696322-BromoacetamideHCID 23665647Potassium tert-butoxideHCID 68567514N-{4-chloro-2-[(3-methoxyphenyl)(hydroxy)methyl]phenyl}-3,4-dimethoxybenzenesulfonamide

Product 1

HCID 58941201N2-{4-chloro-2-[hydroxy(3-methoxyphenyl)methyl]phenyl}-N2-[(3,4-dimethoxyphenyl)sulfonyl]glycinamideYield 50.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.7 g of N-{4-chloro-2-[(3-methoxyphenyl)(hydroxy)methyl]phenyl}-3,4-dimethoxybenzenesulfonamide dissolved in 5 ml of THF are added, at room temperature, 0.2 g of potassium tert-butoxide and 0.25 g of 2-bromoacetamide. After 48 hours at 20° C., the reaction medium is concentrated, 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 0.4 g of the expected product.

Workup

  1. additionare added, at room temperature
  2. concentrationthe reaction medium is concentrated
  3. washwashed with water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on a column of silica gel
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-16c6800fec944a298707f4be9b5e2efc
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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