Acetic Anhydride → HCID 15677066, compound

HRID 1090709Notes

Reaction equation

HRID 1090709 reaction equation
[OH:1][CH:2]([CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25])[CH2:19][CH2:18]1)[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:15])[NH:10]2.[C:31](OC(=O)C)(=[O:33])[CH3:32]>N1C=CC=CC=1>[C:31]([O:1][CH:2]([CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25])[CH2:19][CH2:18]1)[CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:15])[NH:10]2)(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15677026HCID 15677026, compound

Product 1

HCID 15677066HCID 15677066, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,4-Dihydro-5-[2-hydroxy-3-(4-(isobutoxycarbonylamino)-1-piperidyl)propoxy]carbostyril (3 g) was dissolved in pyridine (30 mL) and acetic anhydride (0.9 mL) was added dropwise with stirring. After the addition, the mixture was stirred at room temperature for 12 hours, and the pyridine was then evaporated under reduced pressure. The residue was dissolved in chloroform (100 mL) and the organic solution was washed twice with water (50 mL each) and dried over sodium sulfate. The solvent was then evaporated and the residue recrystallized from isopropyl ether to yield 1.5 g of the title compound, 3,4-dihydro-5-[2-acetyloxy-3-(4-(isobutoxycarbonylamino)-1-piperidyl)propoxy]carbostyril, m.p. 120° C.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. customthe pyridine was then evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform (100 mL)
  5. washthe organic solution was washed twice with water (50 mL each)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was then evaporated
  8. customthe residue recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-5f30bf19fa3b48cf85fec1cea478257c
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

Loading…