Acetic Anhydride → HCID 25029024, compound

HRID 987059Notes

Reaction equation

HRID 987059 reaction equation
[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@H:21]3[O:27][C:25](=[O:26])[CH2:24][C@H:23](O)[CH2:22]3)[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@H:10]([CH3:29])[CH2:9]1)=[O:6])[CH3:4].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[CH3:29][CH:10]1[CH:11]=[C:12]2[CH:13]([CH:14]([CH2:19][CH2:20][CH:21]3[CH2:22][CH:23]=[CH:24][C:25](=[O:26])[O:27]3)[CH:15]([CH3:18])[CH:16]=[CH:17]2)[CH:8]([O:7][C:5](=[O:6])[CH:3]([CH3:4])[CH2:2][CH3:1])[CH2:9]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 53232Lovastatin

Product 1

HCID 25029024HCID 25029024, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 4.0 g (10 mmol) mevinolin in 20 ml pyridine at room temperature are added 20 ml acetic acid anhydride. After 1 h the reaction mixture is concentrated in-vacuo. The residue is dissolved with 10 ml methyl-t-butyl ether and washed successively with water, 0.1 N HCl and brine. The organic phase is then dried over sodium sulfate and the solvent removed in vacuo. The crude product is purified by silica gel chromatography (methyl-t-butyl ether 1/3) to afford 2-methyl-butyric acid 3,7-dimethyl-8-[2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl]-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester) as a white powder.

Workup

  1. concentrationAfter 1 h the reaction mixture is concentrated in-vacuo
  2. dissolutionThe residue is dissolved with 10 ml methyl-t-butyl ether
  3. washwashed successively with water, 0.1 N HCl and brine
  4. dry with materialThe organic phase is then dried over sodium sulfate
  5. customthe solvent removed in vacuo
  6. customThe crude product is purified by silica gel chromatography (methyl-t-butyl ether 1/3)

Sources & evidence

ORD record
ord-ab039fd5714746cd8e15915e339505f7
Source dataset
uspto-grants-2003_10
Patent number
US06630492B1

Reaction notes

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