Water → HCID 67582094, compound

HRID 1416473Notes

Reaction equation

HRID 1416473 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][C@@H:28]3[CH2:32][C@H:31]([O:33]C4CCCCO4)[CH:30]=[CH:29]3)[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>C(O)(=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[N:26]=[C:25]([O:27][C@@H:28]3[CH2:32][C@H:31]([OH:33])[CH:30]=[CH:29]3)[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 21309551HCID 21309551, compound

Product 1

HCID 67582094HCID 67582094, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(1R,4S)-[4-[(RS)-(tetrahydropyran-2-yl)oxy]cyclopent-2-en-1-yl]oxy]quinazoline (12.57 g) in acetic acid (50 ml)--water (12.6 ml) is stirred at 60° C. for 4.5 hours. The reaction mixture is diluted with ethyl acetate and washed with aqueous sodium hydrogen carbonate and 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=500:1, v/v)] to give 2-[4-(benzyloxycarbonyl) piperazin-1-yl]-4-[(1R,4S)-(4-hydroxycyclopent-2-en-1-yl) oxy] quinazoline (6.31 g) as crystals.

Workup

  1. washwashed with aqueous sodium hydrogen carbonate and water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solution is evaporated to dryness under reduced pressure
  4. customthe resulting residue is purified by medium pressure liquid column chromatography [eluent, chloroform

Sources & evidence

ORD record
ord-3a3b016ab78e4c99b58658b82db8bdf3
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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