Hydrochloric Acid → HCID 10019238, compound

HRID 1494121Notes

Reaction equation

HRID 1494121 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[S:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>O1CCCC1>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[S:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 10001566HCID 10001566, compound

Product 1

HCID 10019238HCID 10019238, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.241 g (0.59 mmol) ethyl 8-(2-tetrahydropyranyloxy)-4-[3-(3-pyridyl)propyl]-3thia-octanoate in 1 ml tetrahydrofuran is added 1 mL of 1N hydrochloric acid. After stirring for 1 hour at room temperature, thin layer chromatography indicates incomplete conversion. Another 0.35 mL of 6N hydrochloric acid is added and the mixture is stirred for 1 hour. The pH of the reaction mixture is then adjusted to 8.0 and the resulting solution is extracted with methylene chloride. The organic layer is washed with brine, dried, filtered and evaporated to give yellow oil which is purified by preparative thin layer chromatography over silica gel using ether/ethyl acetate (4:1) as eluent to give ethyl 8-hydroxy-4-[3-(3-pyridyl)propyl]-3-thia-octanoate; IR (CH2Cl2) 3679, 1730 cm-1.

Workup

  1. stirringthe mixture is stirred for 1 hour
  2. extractionthe resulting solution is extracted with methylene chloride
  3. washThe organic layer is washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give yellow oil which
  8. customis purified by preparative thin layer chromatography over silica gel

Sources & evidence

ORD record
ord-ca52e10055c546ada0da9919ea286f40
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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