Ethanol → HCID 67946054, compound

HRID 231601Notes

Reaction equation

HRID 231601 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH3:28])[S:11]([CH:14]=[C:15](C(=O)C)[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1)(=[O:13])=[O:12])[CH3:2].[CH3:30][O:31][C:32](=[O:37])/[CH:33]=[C:34](\[NH2:36])/[CH3:35].[CH2:38](O)[CH3:39]>>[CH3:30][O:31][C:32](=[O:37])[C:33]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:14]([S:11](=[O:12])(=[O:13])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:29])[CH3:28])=[C:38]([CH3:39])[NH:36][C:34]=1[CH3:35]

Participants

4

Reactant 3

HCID 702EthanolHCID 643918Methyl 3-aminocrotonateHCID 54518293HCID 54518293, compound

Product 1

HCID 67946054HCID 67946054, compoundYield 65%

Procedure

A solution of 4.27 g (0.01 mol) of 6-(α-acetyl-N-methyl-3-nitrostyrenesulfonamido)caproic acid ethyl ester in 30 ml of ethanol 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 analogously to Example 1. After chromatography on silica gel with methylene chloride/ethyl acetate (9:1) as the elution agent the crude product is recrystallized from methylene chloride/ether. There are obtained 3.4 g (65%) of 5-{[5-(ethoxycarbonyl)pentyl]methylsulfamoyl}-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid methyl ester, m.p. 83°-86°, 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 methylene chloride/ether

Sources & evidence

ORD record
ord-c2ab22ae7dd74f04b272ed7814a385d7
Source dataset
uspto-grants-1989_07
Patent number
US04847273

Reaction notes

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