Hydrochloric Acid → HCID 53903162, compound

HRID 234845Notes

Reaction equation

HRID 234845 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:15][OH:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=[O:14].[OH-].[Na+].C(=O)(O)[O-].[Na+].[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[S:34](Cl)(=[O:36])=[O:35].S([O-])(O)(=O)=O.[K+]>CO.O.O1CCOCC1>[OH:16][CH2:15][C@H:3]([NH:2][S:34]([C:25]1[CH:26]=[CH:27][C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=1)(=[O:36])=[O:35])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=[O:14]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 71252-Naphthalenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 54175626HCID 54175626, compound

Product 1

HCID 53903162HCID 53903162, compoundYield 74.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2.5 g of the product from b) in 30 ml of methanol is treated with 36 ml of 2N hydrochloric acid and stirred overnight. After evaporation of the solvent the residue is azeotroped with toluene. 1.56 g of the resulting 1-[(R)-2-amino-3-hydroxypropyl]-2-indolinone are dissolved in 2 equivalents of 1N sodium hydroxide solution. Thereto there are added 0.8 g of sodium bicarbonate in 8.1 ml of water and subsequently a solution of 1.46 g of 2-naphthylsulphonyl chloride in 28 ml of dioxan and the mixture is stirred overnight. The reaction mixture is poured into 200 ml of aqueous 5% potassium hydrogen sulphate/10% potassium sulphate and extracted with ethyl acetate. After washing the .organic phase with water and drying the solvent is distilled off. The residue is purified over silica gel with methylene chloride/methanol (98/2). There are obtained 1.9 g of N-[(R)-2-hydroxy-1-(2-oxo-1-indolinylmethyl)ethyl]-2-naphthylsulfonamide.

Workup

  1. customAfter evaporation of the solvent the residue
  2. customis azeotroped with toluene
  3. extractionextracted with ethyl acetate
  4. washAfter washing the .organic phase with water
  5. customdrying the solvent
  6. distillationis distilled off
  7. customThe residue is purified over silica gel with methylene chloride/methanol (98/2)

Sources & evidence

ORD record
ord-969990a7a73d4479bf75419757ff5373
Source dataset
uspto-grants-1997_01
Patent number
US05595999

Reaction notes

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