Water → HCID 20077199, compound

HRID 1654956Notes

Reaction equation

HRID 1654956 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([CH2:16][NH:17]C(OC(C)(C)C)=O)[CH2:10]2)[CH3:2].FC(F)(F)C(O)=O.O.C(=O)([O-])[O-].[K+].[K+].[C:40]1([S:46](Cl)(=[O:48])=[O:47])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([CH2:16][NH:17][S:46]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)(=[O:48])=[O:47])[CH2:10]2)[CH3:2]

Participants

7

Reactant 5

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 7369Benzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 20077201HCID 20077201, compound

Product 1

HCID 20077199HCID 20077199, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.77 g (5.00 mmol) of ethyl[2-(t-butoxycarbonylaminomethyl)-indan-5-oxy]acetate was dissolved in 6 ml of methylene chloride, to which was added 4 ml of trifluoroacetic acid under ice-cooling and stirred for 1 hour. The reaction mixture was diluted with 40 ml of methylene chloride. A solution of 40 ml water containing 8.37 g (60 mmol) of potassium carbonate was added thereto and stirred vigorously. 10 minutes after, 1.07 g (6.00 mmol) of phenylsulfonylchloride was added thereto, and stirred for further 1.5 hours. The organic phase was collected, dried and condensed, and the residue was purified by column gel chromatography (ethyl acetate:hexane=1:1) to obtain 1.68 g of a colorless oil. Yield: 88%

Workup

  1. temperaturecooling
  2. stirringstirred vigorously
  3. stirringstirred for further 1.5 hours
  4. customThe organic phase was collected
  5. customdried
  6. customcondensed
  7. customthe residue was purified by column gel chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-d53fa2b548e04dd58792d3dfe7848403
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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