Water → HCID 57682905, compound

HRID 494995Notes

Reaction equation

HRID 494995 reaction equation
C([OH:5])(C)(C)C.[OH2:6].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(OC)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+].[CH2:71]([C:74]1[C:83]2[O:82][C:81](=[O:84])[N:80]([CH3:85])[CH2:79][C:78]=2[CH:77]=[CH:76][C:75]=1[O:86][CH3:87])[CH:72]=[CH2:73]>C(Cl)(Cl)Cl>[OH:6][CH:72]([CH2:73][OH:5])[CH2:71][C:74]1[C:83]2[O:82][C:81](=[O:84])[N:80]([CH3:85])[CH2:79][C:78]=2[CH:77]=[CH:76][C:75]=1[O:86][CH3:87]

Participants

7

Reactant 5

HCID 962Water2×HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 57682862HCID 57682862, compound

Product 1

HCID 57682905HCID 57682905, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

12 ml of t-butanol and 10 ml of water were added to and dissolved in 0.58 g of 8-allyl-7-methoxy-3-methyl-3,4-dihydro-2H-1,3-benzoxazin-2-one. 2.48 g of AD-mix-β was added to this solution, and the obtained mixture was stirred at room temperature overnight. After confirming the disappearance of raw material, 2.97 g of sodium sulfite was added to the reaction solution, and the obtained mixture was then stirred for approximately 45 minutes. Thereafter, water and chloroform were added to the reaction solution, so as to separate an organic layer. The obtained organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol), so as to obtain 0.55 g of the subject compound.

Workup

  1. additionwas added to the reaction solution
  2. stirringthe obtained mixture was then stirred for approximately 45 minutes
  3. customso as to separate an organic layer
  4. washThe obtained organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removing the drying agent
  7. filtrationby filtration
  8. concentrationthe organic layer was concentrated under a reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-328fbf9e45a443e1af1970074b836a40
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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