Methyl 3-aminocrotonate → HCID 67946089, compound

HRID 231600Notes

Reaction equation

HRID 231600 reaction equation
C1(C([C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[CH:10][S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=O)CCCCC1.[CH3:26][O:27][C:28](=[O:33])/[CH:29]=[C:30](\[NH2:32])/[CH3:31]>C(O)(C)C>[CH3:26][O:27][C:28](=[O:33])[C:29]1[CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:10]([S:11](=[O:13])(=[O:12])[N:14]([CH3:16])[CH3:15])=[C:9]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[NH:32][C:30]=1[CH3:31]

Participants

4

Reactant 2

HCID 643918Methyl 3-aminocrotonateHCID 54065899HCID 54065899, compound

Product 1

HCID 67946089HCID 67946089, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 3.67 g (0.01 mol) of α-(cyclohexylcarbonyl)-N,N-dimethyl-3-nitrostyrenesulfonamide in 30 ml of isopropanol is treated with 1.15 g (0.01 mol) of 3-aminocrotonic acid methyl ester and 1.16 g (0.005 mol) of DL-camphor-10-sulfonic acid in accordance with the procedure described in Example 1. After chromatography on silica gel with methylene chloride/ethyl acetate (9:1) as the elution agent the crude product is recrystallized from acetonitrile. There are obtained 1.5 g (32%) of 6-cyclohexyl-5-(dimethylsulfamoyl)-1,4-dihydro-2-methyl-4-(3-nitrophenyl)nicotinic acid methyl ester, m.p. 185°-188°, as a colorless crystalline powder.

Workup

  1. customAfter chromatography on silica gel with methylene chloride/ethyl acetate (9:1) as the elution agent the crude product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c32fc25c28784be896104a475bc9bd7d
Source dataset
uspto-grants-1989_07
Patent number
US04847273

Reaction notes

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