N,N-Diethylethylenediamine → (2S,4EZ)-4-benzylidene-1-([1,1'-biphenyl]-4-ylcarbonyl)-N-[2-(diethylamino)-ethyl]-2-pyrrolidinecarboxamide

HRID 1349030Notes

Reaction equation

HRID 1349030 reaction equation
[CH:1](=[C:8]1[CH2:12][N:11]([C:13]([O:15]C(C)(C)C)=O)[C@H:10]([C:20]([OH:22])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:28]=[CH:27][C:26](C(Cl)=O)=[CH:25][CH:24]=1.[CH2:38]([N:40]([CH2:44][CH3:45])[CH2:41][CH2:42][NH2:43])[CH3:39]>>[CH:1](=[C:8]1[CH2:12][N:11]([C:13]([C:35]2[CH:34]=[CH:33][C:32]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:37][CH:36]=2)=[O:15])[C@H:10]([C:20]([NH:43][CH2:42][CH2:41][N:40]([CH2:44][CH3:45])[CH2:38][CH3:39])=[O:22])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 841514-Phenylbenzoyl chlorideHCID 69250545(2S,4EZ)-4benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 69249160(2S,4EZ)-4-benzylidene-1-([1,1'-biphenyl]-4-ylcarbonyl)-N-[2-(diethylamino)-ethyl]-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, [1,1′-biphenyl]-4-carbonyl chloride, and N1,N1-diethyl-1,2-ethanediamine the title compound was obtained in 90% purity by LC/MS. MS(ESI+): m/z=482.4.

Sources & evidence

ORD record
ord-098589bb298448219eb6516591d07376
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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