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tert-Butanol → HCID 67581923, compound

HRID 1416499
Notes
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Reaction equation

HRID 1416499 reaction equation
CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:22]C)C=C4)N(CC2)C1.[C:59]([OH:63])(C)([CH3:61])[CH3:60].[CH2:64]([O:71][C:72]([N:74]1[CH2:79][CH2:78][N:77]([C:80]2[N:89]=[C:88]([O:90][CH2:91]CC=C)[C:87]3[C:82](=[CH:83][CH:84]=[CH:85][CH:86]=3)[N:81]=2)[CH2:76][CH2:75]1)=[O:73])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1.S([O-])([O-])=O.[Na+].[Na+]>O>[CH2:64]([O:71][C:72]([N:74]1[CH2:79][CH2:78][N:77]([C:80]2[N:89]=[C:88]([O:90][CH2:91][CH2:60][C@@H:59]([OH:63])[CH2:61][OH:22])[C:87]3[C:82](=[CH:83][CH:84]=[CH:85][CH:86]=3)[N:81]=2)[CH2:76][CH2:75]1)=[O:73])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 67582811HCID 67582811, compound

Product 1

HCID 67581923HCID 67581923, compound

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

To a mixture of AD-mix-β (manufactured by Aldrich Co.) (35.0 g), t-butanol (125 ml) and water (125 ml) is added 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(3-buten-1-yl)oxy]quinazoline [cf. Example 57(2)] (10.46 g) with stirring under ice-cooling, and the mixture is stirred under ice-cooling for 60.5 hours. To the reaction mixture is added sodium sulfite (37.5 g), and the mixture is stirred at room temperature for 30 minutes. The reaction mixture is separated into an organic layer and an aqueous layer, and the aqueous layer is extracted with ethyl acetate. The organic layer is combined with the ethyl acetate extract, and washed with water. The ethyl acetate solution is dried over anhydrous magnesium sulfate, evaporated to dryness under reduced pressure, and the residue is purified by medium pressure liquid column chromatography [eluent, chloroform, (chloroform:methanol=50:1, v/v)], and the resulting crystalline product is recrystallized twice from acetone-diethyl ether to give 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(3R)-(3,4-dihydroxybutan-1-yl)oxy]quinazoline (4.53 g) as crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred under ice-
  3. temperaturecooling for 60.5 hours
  4. stirringthe mixture is stirred at room temperature for 30 minutes
  5. customThe reaction mixture is separated into an organic layer
  6. extractionan aqueous layer, and the aqueous layer is extracted with ethyl acetate
  7. extractionextract
  8. washwashed with water
  9. dry with materialThe ethyl acetate solution is dried over anhydrous magnesium sulfate
  10. customevaporated to dryness under reduced pressure
  11. customthe residue is purified by medium pressure liquid column chromatography [eluent, chloroform
  12. custom(chloroform:methanol=50:1, v/v)], and the resulting crystalline product is recrystallized twice from acetone-diethyl ether

Sources & evidence

ORD record
ord-16f9aa1fd71c4d83bf376783d7328798
Source dataset
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05912247

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes