Diisopropyl Ether → HCID 19009982, compound

HRID 2254141Notes

Reaction equation

HRID 2254141 reaction equation
C(OC(C)C)(C)C.[CH3:8][C:9]1[N:10]([CH2:44][O:45][CH3:46])[C:11]([CH3:43])=[C:12]([C:32]([O:34]COC(=O)C(C)(C)C)=[O:33])[CH:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:14]=1[C:15]([O:17][CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[O:16]>O>[CH3:43][C:11]1[N:10]([CH2:44][O:45][CH3:46])[C:9]([CH3:8])=[C:14]([C:15]([O:17][CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:22])([CH3:23])[CH3:24])=[O:16])[CH:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]=1[C:32]([OH:34])=[O:33]

Participants

4

Reactant 2

HCID 7914Diisopropyl EtherHCID 15004121HCID 15004121, compound

Product 1

HCID 19009982HCID 19009982, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To 20 ml of isopropyl ether saturated with water were added 545 mg of bis(pivaloyloxymethyl) 1,4-dihydro -2,6-dimethyl-1-methoxymethyl-4-phenyl-3,5-pyridinedicarboxylate obtained in Example 10 and 100 mg of Lipase B, and the system was stirred at 25° C. for 5 hours. Any insoluble matter was removed by filtration and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate/hexane=1/1) to obtain 328 mg (yield: 76%) of (+)-1,4-dihydro-2,6-dimethyl-1-methoxymethyl -4-phenyl-5-pivaloyloxymethoxycarbonyl -3-pyridinecarboxylic acid as a colorless crystal.

Workup

  1. customAny insoluble matter was removed by filtration
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-96a46f2ac4254ad68c785ca0131a24bb
Source dataset
uspto-grants-1993_08
Patent number
US05234821

Reaction notes

Loading…