Sodium Hydroxide → HCID 67582038, compound

HRID 1416468Notes

Reaction equation

HRID 1416468 reaction equation
C([O:4][C@@H:5]1[CH2:9][C@H:8]([O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([N:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:28])[CH2:23][CH2:22]3)[N:12]=2)[CH:7]=[CH:6]1)(=O)C.[OH-].[Na+]>CC(C)=O>[CH2:30]([O:29][C:27]([N:24]1[CH2:23][CH2:22][N:21]([C:13]2[N:12]=[C:11]([O:10][C@H:8]3[CH2:9][C@@H:5]([OH:4])[CH:6]=[CH:7]3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH2:26][CH2:25]1)=[O:28])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67582301HCID 67582301, compound

Product 1

HCID 67582038HCID 67582038, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-[(1S,4R)-(4-acetoxycyclopent-2-en-1-yl)oxy]-2-[4-(benzyloxycarbonyl)piperazin-1-yl]quinazoline (2.30 g) and 2N aqueous sodium hydroxide (4.9 ml) in acetone (20 ml) is stirred at room temperature for 18 hours. Acetone is distilled off from the reaction mixture under reduced pressure, and thereto is added ethyl acetate, and the mixture is washed with water, and then dried over anhydrous magnesium sulfate. The solution is evaporated to dryness under reduced pressure, and the resulting residue is purified by medium pressure liquid column chromatography [eluent, chloroform, (chloroform:methanol=200 1, v/v)] to give 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(1S,4R)-(4-hydroxycyclopent-2-en-1-yl)oxy]quinazoline (1.26 g) as crystals.

Workup

  1. distillationAcetone is distilled off from the reaction mixture under reduced pressure
  2. additionis added ethyl acetate
  3. washthe mixture is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solution is evaporated to dryness under reduced pressure
  6. customthe resulting residue is purified by medium pressure liquid column chromatography [eluent, chloroform

Sources & evidence

ORD record
ord-2ffba82a9998411ea621edb1a773eb29
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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