Hydrochloric Acid → HCID 59463458, compound

HRID 1713056Notes

Reaction equation

HRID 1713056 reaction equation
[C:1]1([C:7]2[O:15][C:14]3[CH:13]=[C:12]([C:16]([OH:18])=[O:17])[NH:11][CH2:10][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1([S:27]SC(=O)C)C=CC=CC=1.Cl>CN(C=O)C.O>[SH:27][C:13]1[C:14]2[O:15][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][C:9]=2[CH2:10][NH:11][C:12]=1[C:16]([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 24758Sodium hydrideHCID 53249325Phenylacetyl disulfideHCID 59463441HCID 59463441, compound

Product 1

HCID 59463458HCID 59463458, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

As depicted in Scheme 35 below, 2-phenyl-4,5-dihydro-furo[3,2-c]pyridine-6-carboxylic acid (0.015 mol) is added in portions to a mixture of sodium hydride (60% dispersion in mineral oil, 0.045 mol) in anhydrous DMF (35 ml) under a nitrogen stream at 0° C. After 15 minutes phenylacetyl disulfide (0.02 mol) is added portion-wise, and the reaction is then heated to 50° C. and kept at that temperature overnight. The reaction mixture is then cooled to room temperature and poured onto crushed ice, turned acidic with 2N HCl, and extracted with ethyl acetate. The organic phase is separated, washed with brine, and dried over Na2SO4. The solvent is evaporated under reduced pressure and the obtained residue is triturated with hexane and filtered. The obtained crude residue is then refluxed in the presence of HCl 6N and water to give 7-mercapto-2-phenyl-4,5-dihydro-furo[3,2-c]pyridine-6-carboxylic acid.

Workup

  1. customkept at that temperature overnight
  2. temperatureThe reaction mixture is then cooled to room temperature
  3. additionpoured
  4. customonto crushed ice
  5. extractionextracted with ethyl acetate
  6. customThe organic phase is separated
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. customThe solvent is evaporated under reduced pressure
  10. customthe obtained residue is triturated with hexane
  11. filtrationfiltered
  12. customThe obtained crude residue

Sources & evidence

ORD record
ord-04756aece125457d9a21d88a0697af88
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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