Hydrochloric Acid → HCID 135773208, compound

HRID 904693Notes

Reaction equation

HRID 904693 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([OH:20])=[O:19])[CH:8]=[C:7]2[NH:21][CH2:22][CH3:23])(=[O:3])[CH3:2].Cl.O.[CH2:26](O)[CH3:27]>>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH2:26][CH3:27])=[O:19])[CH:8]=[C:7]2[NH:21][CH2:22][CH3:23])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 135773200HCID 135773200, compound

Product 1

HCID 135773208HCID 135773208, compound

Procedure

The product of step (a) in ethanol was saturated with hydrogen chloride gas and, when the heat of solvation subsided, the brown solution was heated to reflux on a steambath for 5 hours. The mixture was cooled and was treated with water, then concentrated and the pH of the mixture was adjusted to about 7 before extracting into ethyl acetate. The extract was washed with water, dried and evaporated to give a yellowish solid (6.2 g; 82%). NMR and mass spectra were consistent with the required structure.

Workup

  1. temperatureheat of solvation
  2. temperaturethe brown solution was heated
  3. temperatureto reflux on a steambath for 5 hours
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated
  6. extractionbefore extracting into ethyl acetate
  7. washThe extract was washed with water
  8. customdried
  9. customevaporated
  10. customto give a yellowish solid (6.2 g; 82%)

Sources & evidence

ORD record
ord-894491307224456f9ed7cc44adad19ac
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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