Methanol → HCID 178496727, compound

HRID 991143Notes

Reaction equation

HRID 991143 reaction equation
[CH3:1][C:2]1([CH3:33])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]([O:22][C:23](=[O:25])[CH3:24])[C@@H:15]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[O:14][C@@H:13]2Br)[CH3:10])[C:4](=[O:32])[CH2:3]1.[CH3:34][OH:35]>FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:1][C:2]1([CH3:33])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]([O:22][C:23](=[O:25])[CH3:24])[C@@H:15]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[O:14][C@H:13]2[O:35][CH3:34])[CH3:10])[C:4](=[O:32])[CH2:3]1

Participants

4

Reactant 2

HCID 887MethanolHCID 178476345HCID 178476345, compound

Product 1

HCID 178496727HCID 178496727, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 76223Silver(I) trifluoromethanesulfonateCatalyst

Conditions

Temperature
-15 °C

Procedure

2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide (60 mg, 0.11 mmol) was dissolved in CH2C12 (5 ml), cooled to −15° C. and silver trifluoro-methanesulphonate (43 mg, 0.16 mmol) in MeOH (1 ml) added. The reaction mixture was stirred overnight, filtered and the filtrate evaporated. The residue was washed with saturated NaHCO3 solution, dried over MgSO4 and evaporated. The residue was purified by chromatography, to give Methyl 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-3,4,6-tri-O-acetyl-β-D-glucopyranoside (4) (40 mg, 75%).

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated
  3. washThe residue was washed with saturated NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-c3ce45e343134be7a75671a33ba9adbc
Source dataset
uspto-grants-2002_10
Patent number
US06462183B1

Reaction notes

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