Sodium Methoxide → HCID 66696768, compound

HRID 560961Notes

Reaction equation

HRID 560961 reaction equation
ClCC([O:5][C@@H:6]1[C@@H:19]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C@H:18]([F:27])[C@@H:17]([CH2:28][O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[O:16][C@H:7]1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.C[O-].[Na+]>CO>[F:27][C@@H:18]1[C@@H:17]([CH2:28][O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[O:16][C@@H:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@H:6]([OH:5])[C@H:19]1[O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86634493Benzyl 2-O-chloroacetyl-4-deoxy-4-fluoro-3,6-di-O-pivaloyl-beta-D-glucopyranoside

Product 1

HCID 66696768HCID 66696768, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-15 °C

Procedure

Compound (20) (625 mg, 1.21 mmols) was dissolved in methanol (24.2 ml), and sodium methoxide (13.1 mg, 0.6 mmol) was added to the solution with stirring under an argon stream at −15° C. Disappearance of the material was confirmed by TLC 30 minutes later, and the reaction mixture was neutralized (pH 6-7) with a cation-exchange resin IR-120(+). After the resin was filtered off, the filtrate was concentrated in a vacuum. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:4), giving Compound (21) (in an amount of 395 mg, yield 74%).

Workup

  1. customwas confirmed by TLC 30 minutes
  2. filtrationAfter the resin was filtered off
  3. concentrationthe filtrate was concentrated in a vacuum
  4. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-fee79ec551d34d76b35044defef15cd9
Source dataset
uspto-grants-2011_11
Patent number
US08063202B2

Reaction notes

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