Hydrochloric Acid → HCID 131728142, compound

HRID 2240566Notes

Reaction equation

HRID 2240566 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](C(OO)=O)[CH:5]=[CH:6][CH:7]=1.ClC1C=CC(S[C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([F:29])[CH:27]=3)[N:22]([CH2:30][C:31]([OH:33])=[O:32])[C:21]=2[CH3:34])=CC=1.[S:35]([O-:39])([O-])(=[O:37])=S.[Na+].[Na+].Cl>C(#N)C.C(OCC)(=O)C>[NH4+:22].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:35]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([F:29])[CH:27]=3)[N:22]([CH2:30][C:31]([O-:33])=[O:32])[C:21]=2[CH3:34])(=[O:39])=[O:37])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 57402652{3-[(4-Chlorophenyl)sulfanyl]-5-fluoro-2-methyl-1H-indol-1-yl}acetic acid

Product 1

HCID 131728142HCID 131728142, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Chlorobenzenecarboperoxoic acid (0.4 g) was added to a solution of the product from step c) (0.19 g) in acetonitrile (4 ml). The reaction was stirred for 3 h, 1M aqueous sodium thiosulphate (5 ml) was added and stirred for a further 15 min, 10% aqueous HCl and ethyl acetate were added and the organic phase separated. The aqueous phase was re-extracted with ethyl acetate and the combined organic solution washed with brine, dried and concentrated to a solid which was purified by reverse phase chromatography to give the title compound as a solid (0.12 g)

Workup

  1. stirringstirred for a further 15 min
  2. customthe organic phase separated
  3. extractionThe aqueous phase was re-extracted with ethyl acetate
  4. washthe combined organic solution washed with brine
  5. customdried
  6. concentrationconcentrated to a solid which
  7. customwas purified by reverse phase chromatography

Sources & evidence

ORD record
ord-f580f250e93a485bb5482bbe0ecf91d2
Source dataset
uspto-grants-2010_05
Patent number
US07723373B2

Reaction notes

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