HCID 15004122, compound → HCID 19009972, compound

HRID 2254140Notes

Reaction equation

HRID 2254140 reaction equation
[CH3:1][C:2]1[N:3]([CH2:41][O:42][CH3:43])[C:4]([CH3:40])=[C:5]([C:29]([O:31][CH2:32][O:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:30])[CH:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:28])([F:27])[F:26])[C:7]=1[C:8]([O:10]COC(=O)C(C)(C)C)=[O:9]>C(OC(C)C)(C)C.O>[CH3:1][C:2]1[N:3]([CH2:41][O:42][CH3:43])[C:4]([CH3:40])=[C:5]([C:29]([O:31][CH2:32][O:33][C:34](=[O:39])[C:35]([CH3:36])([CH3:37])[CH3:38])=[O:30])[CH:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:28])([F:26])[F:27])[C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 15004122HCID 15004122, compound

Product 1

HCID 19009972HCID 19009972, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Procedure

In 10 ml of isopropyl ether saturated with water was dissolved 613 mg of bis(pivaloyloxymethyl) 1,4-dihydro -2,6-dimethyl-1-methoxymethyl-4-(2-trifluoromethylphenyl)-3,5-pyridinedicarboxylate obtained in Example 8, and 50 mg of Lipase B was added thereto, followed by stirring at room temperature for 7 hours. Any insoluble matter was removed by filtration and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The residue was subjected to preparative TLC (acetate/hexane=1/1), and the spot of the desired product was extracted with ethyl acetate. The extract with concentrated under reduced pressure to obtain 414 mg (yield: 84%) of (+)-1,4-dihydro-2,6-dimethyl -1-methoxymethyl-4-(trifluoromethylphenyl)-5-pivaloyloxymethoxycarbonyl -3-pyridinecarboxylic acid as a colorless crystal.

Workup

  1. additionwas added
  2. customAny insoluble matter was removed by filtration
  3. washwashed with dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. extractionthe spot of the desired product was extracted with ethyl acetate
  6. extractionThe extract
  7. concentrationwith concentrated under reduced pressure

Sources & evidence

ORD record
ord-17fc6ea352834e2491537aabe79d6e4a
Source dataset
uspto-grants-1993_08
Patent number
US05234821

Reaction notes

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