Acetyl chloride → HCID 10517454, compound

HRID 1383619Notes

Reaction equation

HRID 1383619 reaction equation
[OH:1][C@H:2]1[CH2:16][CH:15]=[C:14]2[C@:4]([CH3:17])([CH2:5][C:6]3[C:7](=[CH:13]2)[O:8][C:9](=[O:12])[C:10]=3[CH3:11])[C@H:3]1[CH3:18].[C:19](Cl)(=[O:21])[CH3:20].S([O-])(O)(=O)=O.[K+]>N1C=CC=CC=1>[C:19]([O:1][C@H:2]1[CH2:16][CH:15]=[C:14]2[C@:4]([CH3:17])([CH2:5][C:6]3[C:7](=[CH:13]2)[O:8][C:9](=[O:12])[C:10]=3[CH3:11])[C@H:3]1[CH3:18])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516920Potassium bisulfateHCID 10514571HCID 10514571, compound

Product 1

HCID 10517454HCID 10517454, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

The compound prepared in Example B1 (in the general formula (II), R3=H, R4=CH3, and R5=H) (50 mg, 0.20 mmol) was dissolved in pyridine (5 ml), acetyl chloride (80 mg, 0.70 mmol) was added thereto, and the mixture was stirred at 25° C. for one hr. A 15% aqueous potassium hydrogensulfate solution was added to the reaction solution, followed by extraction with methylene chloride. The organic layer was washed with saturated saline and dried over magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to give the title compound (55 mg, 80%).

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f35c0377f91243f1a1e5a65a099dcd23
Source dataset
uspto-grants-2001_07
Patent number
US06255339B1

Reaction notes

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