Citric Acid → HCID 66766137, compound

HRID 556780Notes

Reaction equation

HRID 556780 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[C:10]3[CH:17]=[C:16]([C@@H:18]4[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]4[OH:20])[CH:15]=[CH:14][C:11]=3[S:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC1C=C(C)C=C(C)N=1>[C:1]1([CH2:7][CH2:8][C:9]2[C:10]3[CH:17]=[C:16]([C@@H:18]4[O:26][C@H:25]([CH2:27][O:28][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C@@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]4[OH:20])[CH:15]=[CH:14][C:11]=3[S:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 10928Ethyl chloroformateHCID 11361588HCID 11361588, compound

Product 1

HCID 66766137HCID 66766137, compound

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To a solution of 1-[3-(2-phenylethyl)benzo[b]-thiophen-5-yl]-1-deoxy-β-D-glucopyranose (0.19 g) in 2,4,6-trimethylpyridine (2 mL) was added ethyl chloroform ate (1.1 mL) at 0° C., and the mixture was stirred at room temperature for 7 hours. The reaction mixture was poured into 10% citric acid aqueous solution, and the mixture was extracted with ethyl acetate. The organic layer washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1) to give the title compound (0.16 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed
  5. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1)

Sources & evidence

ORD record
ord-299e5f4815864089a9f051b19c848ff0
Source dataset
uspto-grants-2011_11
Patent number
US08058245B2

Reaction notes

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