Benzylamine → HCID 69328986, compound

HRID 987058Notes

Reaction equation

HRID 987058 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]([OH:28])[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].[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1.COC(C)(C)C>[CH2:30]([NH:37][C:25]([CH2:24][CH:23]([OH:28])[CH2:22][CH:21]([OH:27])[CH2:20][CH2:19][CH:14]1[CH:13]2[C:12](=[CH:11][CH:10]([CH3:29])[CH2:9][CH:8]2[O:7][C:5](=[O:6])[CH:3]([CH3:4])[CH2:2][CH3:1])[CH:17]=[CH:16][CH:15]1[CH3:18])=[O:26])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 53232Lovastatin

Product 1

HCID 69328986HCID 69328986, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 0.13 g (0.32 mmol) of mevinolin in 15 ml of THF are added 0.5 ml (5 mmol) benzylamine. The stirred reaction mixture is heated at reflux for 7 hours. After cooling to room temperature the reaction is diluted with 20 ml of methyl-t-butyl ether and washed successively with 0.1 N HCl and brine. The organic phase is then dried over sodium sulfate and the solvent evaporated. The crude product is purified by silica gel chromatography (ethyl acetate) to afford the desired product as an oil.

Workup

  1. customThe stirred reaction mixture
  2. temperatureis heated
  3. temperatureat reflux for 7 hours
  4. washwashed successively with 0.1 N HCl and brine
  5. dry with materialThe organic phase is then dried over sodium sulfate
  6. customthe solvent evaporated
  7. customThe crude product is purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-4619380013214bbca2dcd4bc63676d2f
Source dataset
uspto-grants-2003_10
Patent number
US06630492B1

Reaction notes

Loading…