Water → HCID 21961225, compound

HRID 1445325Notes

Reaction equation

HRID 1445325 reaction equation
[OH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[O:8].C([O:20][CH2:21][CH:22]1[CH:27]([O:28]C(=O)C)[CH:26]([O:32]C(=O)C)[CH:25]([O:36]C(=O)C)[CH:24](Br)[O:23]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].O>ClCCl.[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]([C:3]2[S:4][CH:5]=[CH:6][C:2]=2[O:1][CH:24]2[CH:25]([OH:36])[CH:26]([OH:32])[CH:27]([OH:28])[CH:22]([CH2:21][OH:20])[O:23]2)=[O:8])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 102932alpha-D-Galactopyranosyl bromide, tetraacetateHCID 135744175647833-71-4

Product 1

HCID 21961225HCID 21961225, compound

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

2.8 g of (3-hydroxythiophen-2-yl)-(4-methoxy-phenyl)-methanone were dissolved in 350 ml of dichloromethane, and 12.64 g of 3,4,5-triacetoxy-6-bromo-tetrahydropyran-2-ylmethyl actate, 15.4 g of potassium carbonate, 3.6 g of benzyltributylamonium chloride and finally 3 ml of water were added. The mixture was vigorously stirred at room temp. for 20 h. After the reaction was complete, the residue after filtration and concentration was filtered through SiO2 with ethyl acetate/heptane'1:2. The solvent was removed and the residue was taken up in about 300 ml of methanol and, after addition of 35 ml of 1 N NaOCH3 solution in methanol, stirred at room temp. for 1 h. This was followed by neutralization with 7% methanolic hydrochloric acid (about 35 ml), addition of about 100 of dichloromethane/methanol/conc. ammonia=30:5:0.1 mobile phase mixture and stirring for 5 min. This was followed by concentration, taking up the residue with the same mobile phase mixture and removing insoluble salt from the solution. Chromatography on silica gel results in the product with the molecular weight of 396.42 (C18H20O8S), MS (ESI): 397 (M+H+), 235 (M+H+-gluc).

Workup

  1. filtrationthe residue after filtration and concentration
  2. filtrationwas filtered through SiO2 with ethyl acetate/heptane'1
  3. customThe solvent was removed
  4. additionafter addition of 35 ml of 1 N NaOCH3 solution in methanol
  5. stirringstirred at room temp. for 1 h
  6. additionThis was followed by neutralization with 7% methanolic hydrochloric acid (about 35 ml), addition of about 100 of dichloromethane/methanol/conc
  7. stirringammonia=30:5:0.1 mobile phase mixture and stirring for 5 min
  8. concentrationThis was followed by concentration
  9. customremoving insoluble salt from the solution
  10. customChromatography on silica gel results in the product with the molecular weight of 396.42 (C18H20O8S), MS (ESI)

Sources & evidence

ORD record
ord-aa9452915c574e41b3f80a01e7406481
Source dataset
uspto-grants-2010_02
Patent number
US07666848B2

Reaction notes

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