Acetic Acid → HCID 15004132, compound

HRID 1742124Notes

Reaction equation

HRID 1742124 reaction equation
[CH3:1][C:2]1[N:3]([CH2:32][O:33][CH3:34])[C:4]([CH3:31])=[C:5]([C:20]([O:22][CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:21])[C@@H:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]=1[C:8]([OH:10])=[O:9].[N+](=[CH2:37])=[N-].C(O)(=O)C>ClCCl.C(OCC)C>[CH3:1][C:2]1[N:3]([CH2:32][O:33][CH3:34])[C:4]([CH3:31])=[C:5]([C:20]([O:22][CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:27])([CH3:28])[CH3:29])=[O:21])[C@@H:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]=1[C:8]([O:10][CH3:37])=[O:9]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 11102845HCID 11102845, compound

Product 1

HCID 15004132HCID 15004132, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

In 2 ml of dichloromethane was dissolved 476 mg of (S)-1,4-dihydro-2,6-dimethyl-1-methoxymethyl-4-(3-nitrophenyl)-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid obtained in Example 3 or 4, and 6 ml of a 0.5M solution of diazomethane in diethyl ether was added to the solution under cooling with ice, followed by stirring for 1 hour. Acetic acid was added to the reaction mixture until the yellow color disappeared, and the reaction mixture was concentrated. The residue was purified by short silica gel column chromatography (ethyl acetate/hexane=1/3) to give 460 mg (yield: 94%) of (S)-methyl pivaloyloxymethyl 1,4-dihydro-2,6- dimethyl-1-methoxymethyl-4-(3-nitrophenyl)-3,5-pyridinedi-carboxylate as a pale yellow crystal.

Workup

  1. additionwas added to the solution
  2. temperatureunder cooling with ice
  3. concentrationthe reaction mixture was concentrated
  4. customThe residue was purified by short silica gel column chromatography (ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-bca695e428a346f08b709f7fef86f9f1
Source dataset
uspto-grants-1994_08
Patent number
US05336774

Reaction notes

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