Water → HCID 19880359, compound

HRID 1885236Notes

Reaction equation

HRID 1885236 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([OH:17])=[C:11]([CH3:18])[C:10]=1[CH2:19][CH2:20][C:21]([OH:39])([CH3:38])[CH2:22][O:23][C:24]1[CH:37]=[CH:36][C:27]([CH2:28][CH:29]2[S:33][C:32](=[O:34])[NH:31][C:30]2=[O:35])=[CH:26][CH:25]=1.N1[CH:45]=[CH:44]C=CC=1.[OH2:46]>>[C:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][C:44](=[O:46])[CH3:45])=[C:11]([CH3:18])[C:10]=1[CH2:19][CH2:20][C:21]([OH:39])([CH3:38])[CH2:22][O:23][C:24]1[CH:37]=[CH:36][C:27]([CH2:28][CH:29]2[S:33][C:32](=[O:34])[NH:31][C:30]2=[O:35])=[CH:26][CH:25]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 19880358HCID 19880358, compound

Product 1

HCID 19880359HCID 19880359, compound

Procedure

0.8 g of acetic anhydride was added to a mixture of 0.9 g of 5-{4-[4-(2,5-dihydroxy-3,4,6-trimethylphenyl)-2-hydroxy-2-methylbutoxy]benzyl}-2,4-dioxothiazolidine (prepared as described in Example 3) and 7 ml of pyridine, and the resulting mixture was allowed to stand at room temperature for 3 days. At the end of this time, the reaction mixture was poured into 50 ml of water and then extracted with ethyl acetate. The extracts were washed, in turn, with 0.1N aqueous hydrochloric acid and with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure. The resulting residue was then subjected to column chromatography through silica gel, using a 7:3 by volume mixture of benzene and ethyl acetate as the eluent, to afford 0.3 g of the title compound as a white powder softening at 94°-97° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed, in turn, with 0.1N aqueous hydrochloric acid and with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was then removed by distillation under reduced pressure
  5. additionby volume mixture of benzene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-291eb4bcbf7e47298baed1361f93b444
Source dataset
uspto-grants-1992_09
Patent number
US05143930

Reaction notes

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