Hydrochloric Acid → HCID 13336746, compound

HRID 1462903Notes

Reaction equation

HRID 1462903 reaction equation
C1(NC2CCCCC2)CCCCC1.[C:14]([S:22][CH2:23][CH2:24][C:25]([N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][C@@H:28]1[C:37]([OH:39])=[O:38])=[O:26])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.C(O)CC>CC(O)C>[C:14]([S:22][CH2:23][CH2:24][C:25]([N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][C@@H:28]1[C:37]([OH:39])=[O:38])=[O:26])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10311-PropanolHCID 86739570HCID 86739570, compound

Product 1

HCID 13336746HCID 13336746, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The (R)(+)-1-(3-benzoylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid dicyclohexylamine salt thus obtained (4.1 g) was suspended in 2-propanol (25 ml) and this mixture was cooled to 5° and treated with a solution of dry hydrogen chloride in 2 propanol unit pH 2. The resulting dicyclohexylamine hydrochloride was filtered and washed twice with 2-propanol. The combined filtrate and washings were concentrated under reduced pressure. The residue was dissolved in ether (30 ml) and filtered and evaporated. This residue in 2-propanol (25 ml) was cooled to 5° and the pH adjusted to 6-7 with 2% sodium hydroxide in ethanol. The product was collected by filtration, washed with 2-propanol, and then ether. The yield of (R)(+)-1-(3-benzoylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid sodium salt was 2.0 g, m.p. 140°-144°, [α]D20 +221.3° (c 1, methanol).

Workup

  1. temperaturethis mixture was cooled to 5°
  2. filtrationThe resulting dicyclohexylamine hydrochloride was filtered
  3. washwashed twice with 2-propanol
  4. concentrationThe combined filtrate and washings were concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ether (30 ml)
  6. filtrationfiltered
  7. customevaporated
  8. temperatureThis residue in 2-propanol (25 ml) was cooled to 5°
  9. filtrationThe product was collected by filtration
  10. washwashed with 2-propanol

Sources & evidence

ORD record
ord-08d2bf750b9b4f55914daddb9284e61b
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

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