tert-Butanol → HCID 67582099, compound

HRID 1416496Notes

Reaction equation

HRID 1416496 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

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazineHCID 67582811HCID 67582811, compound

Product 1

HCID 67582099HCID 67582099, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of AD-mix-α (manufactured by Aldrich Co.) (29.74 g), t-butanol (106 ml) and water (106 ml) is added 2-[4-(benzyloxycarbonyl)piperazin-1-yl)-4-[(3-buten-1-yl)oxy]-quinazoline (8.88 g) with stirring under ice-cooling, and the mixture is stirred under ice-cooling for 22 hours. To the reaction mixture is added sodium sulfite (31.8 g), and the mixture is stirred at room temperature for 35 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: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-[(3S)-(3,4-dihydroxybutan-1-yl)oxy]quinazoline (2.15 g) as crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred under ice-
  3. temperaturecooling for 22 hours
  4. stirringthe mixture is stirred at room temperature for 35 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. custommethanol=50:1, v/v), and the resulting crystalline product is recrystallized twice from acetone-diethyl ether

Sources & evidence

ORD record
ord-d4c4dd442d4a4b06b2e8111beb54c059
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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