Acetic Anhydride → HCID 15157477, compound

HRID 2371649Notes

Reaction equation

HRID 2371649 reaction equation
[OH:1][CH:2]([CH2:42][OH:43])[CH2:3][CH2:4][CH2:5][C:6]1([CH2:35][CH2:36][CH2:37][CH:38]([OH:41])[CH2:39][OH:40])[CH2:11][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][C:15]([O:20][CH2:21][CH2:22][CH2:23][O:24][C:25]3[C:34]4[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=4[CH:28]=[CH:27][CH:26]=3)=[C:16]([CH2:17][CH2:18][CH3:19])[C:8]=2[O:7]1.C(O[C:48](=[O:50])[CH3:49])(=O)C>N1C=CC=CC=1.C(OCC)(=O)C>[C:2]([O:41][CH:38]([CH2:39][O:40][C:48](=[O:50])[CH3:49])[CH2:37][CH2:36][CH2:35][C:6]1([CH2:5][CH2:4][CH2:3][CH:2]([O:1][C:10](=[O:12])[CH3:9])[CH2:42][O:43][C:6](=[O:7])[CH3:5])[CH2:11][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][C:15]([O:20][CH2:21][CH2:22][CH2:23][O:24][C:25]3[C:34]4[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=4[CH:28]=[CH:27][CH:26]=3)=[C:16]([CH2:17][CH2:18][CH3:19])[C:8]=2[O:7]1)(=[O:1])[CH3:3]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 15157474HCID 15157474, compound

Product 1

HCID 15157477HCID 15157477, compoundYield 115.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 404 mg (0.708 mmol) of the title product of Example 71 in 4.4 ml of pyridine was added 0.70 ml (7.4 mmol) of acetic anhydride. After stirring overnight at room temperature, the mixture was taken up in ethyl acetate, and washed sequentially with two portions of aqueous sodium bicarbonate, water, and brine. The organic layer was dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure. Chromatography of the residue over silica gel, using 40% ethyl acetate/hexane as the eluent, gave the title compound (314 mg).

Workup

  1. washwashed sequentially with two portions of aqueous sodium bicarbonate, water, and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-5be9ccf2148349ccb43b28cf46e0af06
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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