Methanol → HCID 67753882, compound

HRID 1609059Notes

Reaction equation

HRID 1609059 reaction equation
S(Cl)(Cl)=O.[NH2:5][C@H:6]1[C@@H:10]([CH3:11])[CH2:9][N:8]([C:12]2[C:21]([F:22])=[CH:20][C:19]3[C:23](=[O:29])[C:24]([C:26]([OH:28])=[O:27])=[CH:25][N:17]4[C:18]=3[C:13]=2[CH2:14][CH2:15][N:16]4[CH3:30])[CH2:7]1.[CH3:31]O>>[NH2:5][C@H:6]1[C@@H:10]([CH3:11])[CH2:9][N:8]([C:12]2[C:21]([F:22])=[CH:20][C:19]3[C:23](=[O:29])[C:24]([C:26]([O:28][CH3:31])=[O:27])=[CH:25][N:17]4[C:18]=3[C:13]=2[CH2:14][CH2:15][N:16]4[CH3:30])[CH2:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 9928823HCID 9928823, compound

Product 1

HCID 67753882HCID 67753882, compoundYield 72%

Procedure

2 ml of thionyl chloride was added to 20 ml of methanol while cooling on ice, and then this solution was stirred at room temperature. 358 mg of the compound (30) obtained in Example 5 was added to the solvent, and the solution was heated at reflux for 8 hours. The solvent was removed and 40 ml of chloroform and 20 ml of water were added to the residue. The solution was alkalized with sodium hydrogen carbonate, and the organic layer was dried over magnesium sulfate. The solvent was removed by distillation. To the residue, ether was added and then ethyl acetate was added to form crystals. They were filtered off and washed with ethyl acetate in this order to obtain 270 mg of a title compound (121) (yield: 72%).

Workup

  1. temperaturewhile cooling on ice
  2. temperaturethe solution was heated
  3. temperatureat reflux for 8 hours
  4. customThe solvent was removed
  5. addition40 ml of chloroform and 20 ml of water were added to the residue
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. customThe solvent was removed by distillation
  8. additionTo the residue, ether was added
  9. additionethyl acetate was added
  10. customto form crystals
  11. filtrationThey were filtered off
  12. washwashed with ethyl acetate in this order

Sources & evidence

ORD record
ord-6ddcf7932f774586bb1940f30a32a178
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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