Succinic anhydride → Diisopropylethylamine

HRID 1790550Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:28]([O:30][CH3:31])=[O:29])[C:11]2[CH:12]=[CH:13][C:14]([O:26][CH3:27])=[C:15]([NH:17][C:18](CCCC(O)=O)=[O:19])[CH:16]=2)=[CH:5][CH:4]=1)#[N:2].[C:32]1(=O)[O:37][C:35](=[O:36])[CH2:34][CH2:33]1>>[CH3:32][CH2:33][N:9]([CH:6]([CH3:5])[CH3:7])[CH:10]([CH3:11])[CH3:28].[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:28]([O:30][CH3:31])=[O:29])[C:11]2[CH:12]=[CH:13][C:14]([O:26][CH3:27])=[C:15]([NH:17][C:18](=[O:19])[CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH:16]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

Reactant 2

HCID 7922Succinic anhydride

HCID 22040206HCID 22040206, compound

Product 2

HCID 81531Diisopropylethylamine

HCID 22038928HCID 22038928, compound

Procedure

In analogy to Example 70.4–6, from the methyl (RS)-(3-amino-4-methoxy-phenyl)-(4-cyano-phenylamino)-acetate described in Example 70.3, succinic anhydride and Hünig's base there was obtained (RS)-N-{5-[(4-cyano-phenylamino)-methoxycarbonyl-methyl]-2-methoxy-phenyl}-succinamidic acid, which was subsequently converted via (RS)-N-{5-[carboxy-(4-cyano-phenylamino)-methyl]-2-methoxy-phenyl}-succinamidic acid into (RS)-(E)- and/or -(Z)-N-(5-{carboxy-[4-(N-hydroxycarbamimidoyl)-phenylamino]-methyl}-2-methoxy-phenyl)-succinamidic acid.

Sources & evidence

ORD record: ord-bf09a1dc06e4487f919dbbc9a6f83e7d
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071212B2

Reaction notes

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