HCID 54493811, compound → HCID 54229544, compound

HRID 1742131Notes

Reaction equation

HRID 1742131 reaction equation
[CH3:1][C:2]1[N:3]([CH2:40][O:41][CH2:42][CH3:43])[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[N:3]([CH2:40][O:41][CH2:42][CH3:43])[C:2]([CH3:1])=[C:7]([C:8]([O:10][CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:15])([CH3:16])[CH3:17])=[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 54493811HCID 54493811, compound

Product 1

HCID 54229544HCID 54229544, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Procedure

In 20 ml of isopropyl ether saturated with water was dissolved 1.2 g of bis(pivaloyloxymethyl) 1,4-dihydro-2,6-dimethyl-1-ethoxymethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate obtained in Example 14, and 200 mg of Lipase B was added thereto, followed by stirring at room temperature for 4 hours. Any insoluble matter was removed by filtration and washed with dichloromethane. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane=1/2) to obtain 840 mg (yield: 83%) of (S)-1,4-dihydro-2,6-dimethylethoxymethyl-4-(3-nitrophenyl)-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 dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ee9ef43b16304c86a7a4cf6ec89fbcc4
Source dataset
uspto-grants-1994_08
Patent number
US05336774

Reaction notes

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