Water → HCID 54716538, compound

HRID 845748Notes

Reaction equation

HRID 845748 reaction equation
[OH:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([N:8]2[C:18]3[C:13](=[CH:14][C:15]([N:19]4[CH2:24][CH2:23][N:22]([C:25](=[O:36])[C:26]5[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=5)[CH2:21][CH2:20]4)=[CH:16][CH:17]=3)[CH2:12]C[C:9]2=[O:10])=[O:7])=[CH:4][CH:3]=1.[C:39](=[O:42])([O-])[O-].[K+].[K+].Cl[CH2:46][C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48].[OH2:57]>CN(C=O)C>[CH2:50]([O:49][C:47]([CH2:46][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[C:18]3[C:13](=[CH:14][C:15]([N:19]4[CH2:20][CH2:21][N:22]([C:25](=[O:36])[C:26]5[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=5)[CH2:23][CH2:24]4)=[CH:16][CH:17]=3)[C:12]([OH:57])=[C:39]([OH:42])[C:9]2=[O:10])=[O:7])=[CH:37][CH:38]=1)=[O:48])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8786Acetic acid, 2-chloro-, phenylmethyl esterHCID 11430Potassium CarbonateHCID 13913536HCID 13913536, compound

Product 1

HCID 54716538HCID 54716538, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-Hydroxybenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihyrocarbostyril (9 g) was suspended in DMF (90 ml). To the suspension were added potassium carbonate (2.82 g) and benzyl monochloroacetate (3.81 g) and the mixture was stirred at room temperature over night. After completion of reaction, the reaciton mixture was poured into water and extracted with dichloromethane. The extract was washed successively with water and saturated saline solution, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography [eluent:dichloromethane:methanol=100:0 to 100:5] to give 1-(4-benzyloxycarbonylmethoxybenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydroxycarbostyril (4.0 g).

Workup

  1. customAfter completion of reaction
  2. extractionextracted with dichloromethane
  3. washThe extract was washed successively with water and saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica-gel column chromatography [eluent:dichloromethane:methanol=100:0 to 100:5]

Sources & evidence

ORD record
ord-2021021cbcd148dcad0db5eb8f57d05f
Source dataset
uspto-grants-1988_07
Patent number
US04760064

Reaction notes

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