Hydrochloric Acid → HCID 19888723, compound

HRID 654239Notes

Reaction equation

HRID 654239 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([CH2:12][NH:13][C:14](=O)[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[OH:16])[CH2:6][CH2:5]2.B.CSC.CO.Cl>O1CCCC1>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([CH2:12][NH:13][CH2:14][CH:15]([OH:16])[C:17]1[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=1)[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 19888689HCID 19888689, compound

Product 1

HCID 19888723HCID 19888723, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the compound obtained in step (i) above (3.2 g, 0.0092 mol) in anhydrous tetrahydrofuran (65 ml) is heated to the reflux temperature under nitrogen atmosphere and a 10M solution of borane-methyl sulfide (2.8 ml, 0.028 mol) and anhydrous tetrahydrofuran (10 ml) are then added thereto. The mixture is refluxed for 4 hours, methanol (30 ml) is slowly added thereto and refluxing is prolonged for an additional hour. lN HCl (60 ml) is then added thereto and the mixture is refluxed for 1 hour, and concentrated under reduced pressure. The residue is taken up in ethyl acetate, the organic solution is washed with ammonium hydroxide and then with water, dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure affording a solid which is washed with isopropyl ether (2.3 g). M.p. 150°-153° C.

Workup

  1. temperatureThe mixture is refluxed for 4 hours
  2. temperaturerefluxing
  3. waitis prolonged for an additional hour
  4. temperaturethe mixture is refluxed for 1 hour
  5. concentrationconcentrated under reduced pressure
  6. washthe organic solution is washed with ammonium hydroxide
  7. dry with materialwith water, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure
  10. customaffording a solid which
  11. washis washed with isopropyl ether (2.3 g)

Sources & evidence

ORD record
ord-1774174e7d864a019e13779ed79fb14f
Source dataset
uspto-grants-1992_07
Patent number
US05130339

Reaction notes

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