Sodium Methoxide → HCID 59557769, compound

HRID 425054Notes

Reaction equation

HRID 425054 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-622395a639374143848eed4ea7a93175
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

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