Sodium Methoxide → HCID 59557769, compound

HRID 1175243Notes

Reaction equation

HRID 1175243 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([CH2:35]Br)=[CH2:34])=[CH:29][CH:28]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:37][O:38]C(=O)C)(=O)C.[CH3:42][O-:43].[Na+]>CO>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C@H:8]2[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:37][OH:38])[O:7]2)=[CH:20][C:21]=1[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([CH2:35][O:43][CH3:42])=[CH2:34])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57684692HCID 57684692, compound

Product 1

HCID 59557769HCID 59557769, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(3-bromoprop-1-en-2-yl)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (intermediate BA) (110 mg, 0.169 mmol) and 4 mL of 0.3M NaOMe in MeOH (freshly-distilled) was stirred at 70° C. for 2.5 h. Then the reaction was quenched with H2O. After removing the volatiles, the aqueous layer was extracted 3× with AcOEt. The organic portion was washed 1× with a saturated solution of NH4Cl and 1× with brine prior to drying over Na2SO4. Concentration and purification of the crude product by preparative TLC gave intermediate BA (48 mg).

Workup

  1. customThen the reaction was quenched with H2O
  2. customAfter removing the volatiles
  3. extractionthe aqueous layer was extracted 3× with AcOEt
  4. washThe organic portion was washed 1× with a saturated solution of NH4Cl and 1× with brine
  5. dry with materialto drying over Na2SO4
  6. concentrationConcentration and purification of the crude product by preparative TLC
  7. customgave intermediate BA (48 mg)

Sources & evidence

ORD record
ord-669b7a11fce443a8bfa0873ad25f234e
Source dataset
uspto-grants-2010_11
Patent number
US07838499B2

Reaction notes

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