p-Chlorophenoxyacetyl chloride → (2S,4EZ)-4-benzylidene-1-[(4-chlorophenoxy)acetyl]-N-(3,4-dimethoxy-benzyl)-2-pyrrolidinecarboxamide

HRID 1349062Notes

Reaction equation

HRID 1349062 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.[Cl:23][C:24]1[CH:34]=[CH:33][C:27]([O:28][CH2:29]C(Cl)=O)=[CH:26][CH:25]=1.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:40][NH2:41]>>[CH:1](=[C:8]1[CH2:12][N:11]([C:13](=[O:15])[CH2:29][O:28][C:27]2[CH:26]=[CH:25][C:24]([Cl:23])=[CH:34][CH:33]=2)[C@H:10]([C:20]([NH:41][CH2:40][C:39]2[CH:42]=[CH:43][C:44]([O:45][CH3:46])=[C:37]([O:36][CH3:35])[CH:38]=2)=[O:22])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 77771p-Chlorophenoxyacetyl chlorideHCID 79832VeratrylamineHCID 69250545(2S,4EZ)-4benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 69455967(2S,4EZ)-4-benzylidene-1-[(4-chlorophenoxy)acetyl]-N-(3,4-dimethoxy-benzyl)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, (4-chlorophenoxy)acetyl chloride, and 3,4-dimethoxybenzylamine the title compound was obtained in 49% purity by LC/MS. MS(ESI+): m/z=521.6.

Sources & evidence

ORD record
ord-953a80198d0a4f21ad037e523a15e658
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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