Acetic Anhydride → 3-Ethyl 5-methyl 4-[3-(acetylamino)phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

HRID 5651Notes

Reaction equation

HRID 5651 reaction equation
[CH3:1][C:2](OC(C)=O)=[O:3].[CH3:8][C:9]1[NH:10][C:11]([CH3:31])=[C:12]([C:27]([O:29][CH3:30])=[O:28])[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[CH:21]=2)[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]>N1C=CC=CC=1>[CH3:8][C:9]1[NH:10][C:11]([CH3:31])=[C:12]([C:27]([O:29][CH3:30])=[O:28])[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:2](=[O:3])[CH3:1])[CH:21]=2)[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15270288HCID 15270288, compound

Product 1

HCID 152702903-Ethyl 5-methyl 4-[3-(acetylamino)phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under inert gas atmosphere Ac2O (43 mcl) is added to a stirred solution of (-)-2,6-dimethyl-3-carboethoxy-5-carbomethoxy-4-(3-aminophenyl)-1,4-dihydropyridine (100 mg) in pyridine (ml 1). 90 minutes after dilution with water (ml 50), extraction with AcOEt (3×10 ml) and crystallization from Et2O 70/EtOH 10, give mg 85 of +)-2,6-dimethyl-3-carboethoxy-5-carbomethoxy-4-(3-acetylaminophenyl)-1,4-dihydropyridine m.p. 197°-199° C. [α]D =+0.87°, [α]578 =+2.00°, [α]546 =+1.64° c=2.2 DMF.

Workup

  1. extraction90 minutes after dilution with water (ml 50), extraction
  2. customwith AcOEt (3×10 ml) and crystallization from Et2O 70/EtOH 10

Sources & evidence

ORD record
ord-9c4c8e8f7f234b989171bc299cf5fb6f
Source dataset
uspto-grants-1993_09
Patent number
US05245039

Reaction notes

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