HCID 11135371, compound → HCID 10993727, compound

HRID 2254136Notes

Reaction equation

HRID 2254136 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:39])=[C:5]([C:28]([O:30]COC(=O)C(C)(C)C)=[O:29])[CH:6]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[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]>C(OC(C)C)(C)C.O>[CH3:39][C:4]1[NH:3][C:2]([CH3:1])=[C:7]([C:8]([O:10][CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:9])[C@@H:6]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:5]=1[C:28]([OH:30])=[O:29]

Participants

4

Reactant 1

HCID 11135371HCID 11135371, compound

Product 1

HCID 10993727HCID 10993727, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Procedure

In 20 ml of isopropyl ether saturated with water was dissolved 546 mg of bis(pivaloyloxymethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl) -3,5-pyridinedicarboxylate obtained in Example 2-(3), and 200 mg of Lipase B was added thereto, followed by stirring at room temeprature for 35 hours. Any insoluble matter was removed by filtration and washed with dichloromethane, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by short silica gel column chromatography (ethyl acetate/hexane=1/3) to obtain 35 mg (yield: 83%) of (S)-1,4-dihydro 2,6-dimethyl-4-(3-nitrophenyl)-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid as a pale yellow crystal.

Workup

  1. addition200 mg of Lipase B was added
  2. customAny insoluble matter was removed by filtration
  3. washwashed with dichloromethane
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by short silica gel column chromatography (ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-03fa8a81147d4968897441aa040d30d1
Source dataset
uspto-grants-1993_08
Patent number
US05234821

Reaction notes

Loading…