Acetic Anhydride → HCID 19028898, compound

HRID 1781500Notes

Reaction equation

HRID 1781500 reaction equation
[NH2:1][CH2:2][C:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][CH2:5][CH2:6][OH:7].[C:20](OC(=O)C)(=[O:22])C>C(O)=O>[CH:20]([NH:1][CH2:2][C:3]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:4][CH2:5][CH2:6][OH:7])=[O:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12429924HCID 12429924, compound

Product 1

HCID 19028898HCID 19028898, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In formic acid (80 ml) was dissolved 5-amino-4,4-diphenylpentanol (10 g) followed by addition of acetic anhydride (13 ml) and the mixture was stirred at room temperature for 4 hours. This reaction mixture was concentrated to dryness and the group was partitioned into chloroform and water. The water layer was made basic by aqueous ammonia and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated to dryness. The group was dissolved in ethanol (30 ml) and the solution was stirred in 1N-aqueous sodium hydroxide (20 ml) at room temperature for 20 minutes. This reaction mixture was diluted with water and the crystals that separated out were harvested by filtration. This crystal crop was washed serially with water and ethyl acetate to provide the title compound (9 g) as colorless powder.

Workup

  1. concentrationThis reaction mixture was concentrated to dryness
  2. customthe group was partitioned into chloroform and water
  3. extractionextracted with chloroform
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. dissolutionThe group was dissolved in ethanol (30 ml)
  7. stirringthe solution was stirred in 1N-aqueous sodium hydroxide (20 ml) at room temperature for 20 minutes
  8. additionThis reaction mixture was diluted with water
  9. customthe crystals that separated out
  10. filtrationwere harvested by filtration
  11. washThis crystal crop was washed serially with water and ethyl acetate

Sources & evidence

ORD record
ord-11164e2e6e7e43489e2df2d0327da2ec
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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