Water → HCID 53726946, compound

HRID 399966Notes

Reaction equation

HRID 399966 reaction equation
[OH:1][C@@H:2]1[C@@:21]2([CH3:22])[C:6](=[CH:7][CH:8]=[C:9]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:23])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:14](=[O:16])[CH3:15])[CH2:5][C@@H:4]([OH:24])[CH2:3]1.[C:25](OC(=O)C)(=[O:27])[CH3:26].[OH2:32].N1[CH:38]=[CH:37]C=CC=1>CN(C)C1C=CN=CC=1>[C:25]([O:1][C@@H:2]1[C@@:21]2([CH3:22])[C:6](=[CH:7][CH:8]=[C:9]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:23])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:14](=[O:16])[CH3:15])[CH2:5][C@@H:4]([O:24][C:37](=[O:32])[CH3:38])[CH2:3]1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 54133031HCID 54133031, compound

Product 1

HCID 53726946HCID 53726946, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of the compound obtained in Example 5 (1.68 g, 5.08 mmol), acetic anhydride (30 ml) and 4-dimethylaminopyridine (DMAP, 60 mg) in pyridine (60 ml) was stirred at room temperature for 4 days. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to give the title compound (1.65 g, 78%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-8505365d898341adbb2b973b07de6c23
Source dataset
uspto-grants-1998_10
Patent number
US05824811

Reaction notes

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