Water → HCID 20077192, compound

HRID 1289444Notes

Reaction equation

HRID 1289444 reaction equation
C(OC([NH:11][CH2:12][CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:19]=2)[CH2:14]1)=O)C1C=CC=CC=1.O.C(=O)([O-])[O-].[K+].[K+].[C:35]1([S:41](Cl)(=[O:43])=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CO.[C].[Pd]>[C:35]1([S:41]([NH:11][CH2:12][CH:13]2[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:19]=3)[CH2:14]2)(=[O:43])=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 20077190HCID 20077190, compound

Product 1

HCID 20077192HCID 20077192, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Dissolved in 30 ml of methanol were 1.80 g (4.90 mmol) of ethyl [2-(benzyloxycarbonylaminomethyl)indan-5-yl]acetate, and 500 mg of 10% palladium-carbon were added to the solution, followed by stirring for 2 hours under a hydrogen atmosphere. The catalyst was separated by filtration, and the filtrate was concentrated. The resultant residue was dissolved in 15 ml of ethyl acetate, and 10 ml of water and 1.18 g (8.51 mmol) of potassium carbonate were added to the solution. While vigorously stirring, 902 mg (5.11 mmol) of benzenesulfonyl chloride were then added dropwise. After the addition, the mixture was stirred for 1 hour, and an organic layer separated was taken out, dried and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform) to obtain 1.78 g of a colorless oily substance. Yield: 97%.

Workup

  1. additionwere added to the solution
  2. customThe catalyst was separated by filtration
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe resultant residue was dissolved in 15 ml of ethyl acetate
  5. stirringWhile vigorously stirring
  6. additionAfter the addition
  7. stirringthe mixture was stirred for 1 hour
  8. customan organic layer separated
  9. customdried
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography on silica gel (chloroform)
  12. customto obtain 1.78 g of a colorless oily substance

Sources & evidence

ORD record
ord-516c33858e434311a534ac8931bc6d14
Source dataset
uspto-grants-1998_05
Patent number
US05750524

Reaction notes

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