N,N-Diethylethylenediamine → (2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]-imino}-N-[2-(diethylamino)ethyl]-2-pyrrolidinecarboxamide

HRID 1349083Notes

Reaction equation

HRID 1349083 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:10][C@H:9]1[C:24]([OH:26])=O)=[O:7])(C)(C)C.[C:27]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:31][C:30](C(Cl)=O)=[CH:29][CH:28]=1.[CH2:42]([N:44]([CH2:48][CH3:49])[CH2:45][CH2:46][NH2:47])[CH3:43]>>[C:36]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:37]=[CH:38][C:39]([C:6]([N:8]2[CH2:12][C:11](=[N:13][O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[CH2:10][C@H:9]2[C:24]([NH:47][CH2:46][CH2:45][N:44]([CH2:48][CH3:49])[CH2:42][CH3:43])=[O:26])=[O:7])=[CH:40][CH:41]=1

Participants

4

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 841514-Phenylbenzoyl chlorideHCID 131725417(2S,4EZ)-1-(tert-butoxycarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]imino}-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725460(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]-imino}-N-[2-(diethylamino)ethyl]-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]imino}-2-pyrrolidinecarboxylic acid, [1,1′-biphenyl]-4-carbonyl chloride, and N1,N1-diethyl-1,2-ethanediamine the title compound was obtained in 74% purity by LC/MS. MS(ESI+): m/z=581.6.

Sources & evidence

ORD record
ord-3c7bbc1690cb4504bc05bc1d0ce8df15
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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