Trifluoroacetic acid → HCID 20077199, compound

HRID 1289449Notes

Reaction equation

HRID 1289449 reaction equation
C(OC([NH:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:16]=2)[CH2:11]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+].[C:39]1([S:45](Cl)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl.O>[C:39]1([S:45]([NH:8][CH2:9][CH:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:16]=3)[CH2:11]2)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7369Benzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 20077201HCID 20077201, compound

Product 1

HCID 20077199HCID 20077199, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Dissolved in 6 ml of methylene chloride were 1.77 g (5.00 mmol) of ethyl [2-(t-butoxycarbonylaminomethyl)indane-5-oxy]acetate, and 4 ml of trifluoroacetic acid were added under chilling with ice water, followed by stirring for 1 hour. The liquid reaction mixture was diluted with 40 ml of methylene chloride, and a solution of 8.37 g (60 mmol) of potassium carbonate in 40 ml of water was added, followed by vigorous stirring. After 10 minutes, 1.07 g (6.00 mmol) of phenyl-sulfonyl chloride were added, and the resultant mixture was stirred further for 1.5 hours. An organic layer separated was taken out, dried and then concentrated, and the residue was purified by column chromatography on silica gel (ethyl acetate: hexane=1:1), thereby obtaining 1.68 g of a colorless oily substance. Yield: 88%.

Workup

  1. additionwere added
  2. customThe liquid reaction mixture
  3. waitAfter 10 minutes
  4. customAn organic layer separated
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography on silica gel (ethyl acetate: hexane=1:1)
  8. customobtaining 1.68 g of a colorless oily substance

Sources & evidence

ORD record
ord-de1270c980db4fe986c4d826d0e82fce
Source dataset
uspto-grants-1998_05
Patent number
US05750524

Reaction notes

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