Hydrochloric Acid → HCID 66968976, compound

HRID 1359928Notes

Reaction equation

HRID 1359928 reaction equation
[OH-].[Na+].[CH:3]1([O:7][C:8]2[CH:13]=[C:12]([C:14]3([O:32][C@H:31]([CH2:33][O:34]C(=O)C)[C@@H:26]([O:27]C(=O)C)[C@H:21]([O:22]C(=O)C)[C@H:16]3[O:17]C(=O)C)[OH:15])[CH:11]=[C:10]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([CH2:45][CH3:46])=[CH:41][CH:40]=3)[C:9]=2[CH3:47])[CH2:6][CH2:5][CH2:4]1.Cl>CO.C1COCC1>[CH:3]1([O:7][C:8]2[CH:13]=[C:12]([C:14]3([O:32][C@H:31]([CH2:33][OH:34])[C@@H:26]([OH:27])[C@H:21]([OH:22])[C@H:16]3[OH:17])[OH:15])[CH:11]=[C:10]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([CH2:45][CH3:46])=[CH:41][CH:40]=3)[C:9]=2[CH3:47])[CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66969084HCID 66969084, compound

Product 1

HCID 66968976HCID 66968976, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide solution (0.15 mL, 4 mol/L) is added to 1-cyclobutoxy-3-(4-ethylbenzyl)-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene (80 mg) dissolved in methanol (1 mL) and THF (0.5 mL). The solution is stirred at room temperature for 1 h and then neutralized with hydrochloric acid (1 mol/L). After removal of the organic solvents, the residue is diluted with aqueous sodium bicarbonate solution and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are dried (sodium sulphate) and the solvent is evaporated. The remainder is purified by chromatography on silica gel (dichloromethane/methanol 1:0->6:1).

Workup

  1. customAfter removal of the organic solvents
  2. additionthe residue is diluted with aqueous sodium bicarbonate solution
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. dry with materialThe combined organic extracts are dried (sodium sulphate)
  5. customthe solvent is evaporated
  6. customThe remainder is purified by chromatography on silica gel (dichloromethane/methanol 1:0->6:1)

Sources & evidence

ORD record
ord-8a2beb21d918496791c4e951b310ecba
Source dataset
uspto-grants-2011_02
Patent number
US07879807B2

Reaction notes

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