Water → HCID 14820516, compound

HRID 1088830Notes

Reaction equation

HRID 1088830 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH2:5]2.C(=O)([O-])O.[Na+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].O>CN(C)P(=O)(N(C)C)N(C)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][CH:6]2[CH2:5][C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:3]=3)[CH2:7]2)(=[O:14])=[O:13])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 60984Methyl bromoacetateHCID 516892Sodium BicarbonateHCID 14820515HCID 14820515, compound

Product 1

HCID 14820516HCID 14820516, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

Into a solution of 0.5 g of 5-amino-2-(4-chlorophenyl)sulfonylaminoindan in 5 ml of hexamethylphosphoric triamide are added 0.2 g of sodium hydrogen carbonate and 0.25 g of methyl bromoacetate at 5 to 10° C., and the mixture is stirred at the same temperature for 4 hours. Water is added to the reaction mixture, followed by extraction with ethyl acetate. The extract is washed, dried and the solvent is evaporated. The residue is purified by separation through silica gel column chromatography (eluant: chloroform : ethyl acetate=7 : 3), and further recrystallized from ethyl acetate-n-hexane mixture to give 0.47 g of methyl N-[2-(4-chlorophenyl)sulfonylaminoindan-5-yl]glycinate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract is washed
  3. customdried
  4. customthe solvent is evaporated
  5. customThe residue is purified by separation through silica gel column chromatography (eluant: chloroform : ethyl acetate=7 : 3)
  6. customfurther recrystallized from ethyl acetate-n-hexane mixture

Sources & evidence

ORD record
ord-1527583dc1524b90a427baeccfd6e80e
Source dataset
uspto-grants-1990_10
Patent number
US04963587

Reaction notes

Loading…