Methanol → HCID 66834157, compound

HRID 2275283Notes

Reaction equation

HRID 2275283 reaction equation
C([SiH2][O:6][C:7](C)(C)[C@@H:8]1[O:12]C(C)(C)[O:10][C@@H:9]1[CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]2[C:32](=[O:33])[C:31]3[C:30]4[N:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:24][C:23]=3[C:22]([CH3:35])([CH3:34])[C:21]=2[CH:36]=1)(C)(C)C.CO.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:34][C:22]1([CH3:35])[C:23]2[O:24][C:25]3[CH:26]=[CH:27][CH:28]=[N:29][C:30]=3[C:31]=2[C:32](=[O:33])[C:20]2[CH:19]=[CH:18][C:17]([O:16][CH2:15][C@@H:9]([OH:10])[C@H:8]([OH:12])[CH2:7][OH:6])=[CH:36][C:21]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 178431644HCID 178431644, compound

Product 1

HCID 66834157HCID 66834157, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
57.5 °C

Procedure

To the mixture of 8-[(4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy]-10,10-dimethyl-10H-11-oxa-4-aza-benzo[b]fluoren-5-one (Compound GT15-6, 27 mg), MeOH (0.1 ml) and THF (0.3 ml), 0.5 N sulfuric acid (0.1 ml) was added, and the mixture was stirred and heated at 55 to 60° C. for 4 hrs. The reaction mixture was neutralized with saturated aqueous solution of sodium bicarbonate. The resulting solid was filtered and washed with diethyl ether. The filtrate was extracted with the mixture solution of DCM and MeOH (DCM:MeOH=10:1). The organic layer was washed with saturated brine, and dried over magnesium sulfate. The filtered solid and the residues obtained after concentration under reduced pressure were combined and purified by silica gel column (DCM/MeOH) to obtain the title compound (5.4 mg, 28%).

Workup

  1. additionwas added
  2. filtrationThe resulting solid was filtered
  3. washwashed with diethyl ether
  4. extractionThe filtrate was extracted with the mixture solution of DCM and MeOH (DCM:MeOH=10:1)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe filtered solid and the residues obtained
  8. concentrationafter concentration under reduced pressure
  9. custompurified by silica gel column (DCM/MeOH)

Sources & evidence

ORD record
ord-5865770bd9ee402d84d239831a8893dd
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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