Diisopropyl Ether → HCID 19010021, compound

HRID 1742135Notes

Reaction equation

HRID 1742135 reaction equation
[CH3:1][C:2]1[NH:3][C:4](C)=[C:5]([C:20]([O:22]COC(=O)C(C)(C)C)=[O:21])[CH:6]([CH3:19])[C:7]=1[C:8]([O:10][CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:9].[CH:32](OC(C)C)(C)C>O>[CH3:32][N:3]1[C:2]([CH3:1])=[C:7]([C:8]([O:10][CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:16])([CH3:15])[CH3:17])=[O:9])[CH:6]([CH3:19])[C:5]([C:20]([OH:22])=[O:21])=[CH:4]1

Participants

4

Reactant 2

HCID 7914Diisopropyl EtherHCID 15327599HCID 15327599, compound

Product 1

HCID 19010021HCID 19010021, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 30 ml of isopropyl ether saturated with water was dissolved 1.32 g of the bis(pivaloyloxymethyl) 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate obtained in Example 18, and 300 mg of Lipase B was added thereto, followed by stirring at room temperature for 8 hours. Any insoluble matter was removed by filtration and washed with acetone. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate/hexane =1/3) to obtain 741 mg (yield: 76%) of (+)-1,4-dihydro-1,4,6-trimethyl-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid as a pale yellow crystal.

Workup

  1. additionwas added
  2. customAny insoluble matter was removed by filtration
  3. washwashed with acetone
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9b62804a8a224f53a9e99d7c335cf71a
Source dataset
uspto-grants-1994_08
Patent number
US05336774

Reaction notes

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