Benzyl crotonate, (E)- → Benzyl [7-{N-(ethoxycarbonyl)amino}-3-(3-methoxy-4-nitrobenzoyl)-2-methylindolizin-1-yl]carboxylate

HRID 1987845Notes

Reaction equation

HRID 1987845 reaction equation
[Br-].[CH2:2]([O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][N+:11]([CH2:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH3:27])[CH:18]=2)=[O:16])=[CH:10][CH:9]=1)=[O:6])[CH3:3].[C:28]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:32])/[CH:29]=[CH:30]/[CH3:31]>[O-2].[Mn+2]>[CH2:2]([O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][N:11]2[C:10]([CH:9]=1)=[C:29]([C:28]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C:30]([CH3:31])=[C:14]2[C:15](=[O:16])[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH3:27])[CH:18]=1)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 5356259Benzyl crotonate, (E)-HCID 866075554-[N-(ethoxycarbonyl)amino]-1-[2-(3-methoxy-4-nitrophenyl)-2-oxoethyl]pyridinium bromide

Product 1

HCID 86607557Benzyl [7-{N-(ethoxycarbonyl)amino}-3-(3-methoxy-4-nitrobenzoyl)-2-methylindolizin-1-yl]carboxylateYield 26%

Reagents, catalysts & solvents 1

HCID 160959Manganese oxideCatalyst

Procedure

This compound is prepared according to the same method as that described in Example 47 Step B from 1.8 g (4.1 mmol) of 4-[N-(ethoxycarbonyl)amino]-1-[2-(3-methoxy-4-nitrophenyl)-2-oxoethyl]pyridinium bromide with benzyl crotonate in the presence of manganese oxide as oxidizing agent. 573 mg of a yellow powder are obtained.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-d5ad3b8667ee4e1cb3475e35f2fcbae8
Source dataset
uspto-grants-2009_06
Patent number
US07553845B2

Reaction notes

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