Allylamine → (2S,4EZ)-N-allyl-4-{[(3,4-dichlorobenzyl)oxy]imino}-(diphenylacetyl)-2-pyrrolidinecarboxamide

HRID 1349077Notes

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([CH:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)C(Cl)=O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH2:43]([NH2:46])[CH:44]=[CH2:45]>>[CH2:43]([NH:46][C:24]([C@@H:9]1[CH2:10][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)[CH2:12][N:8]1[C:6](=[O:7])[CH:33]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:26])[CH:44]=[CH2:45]

Participants

Reactant 3

HCID 7853Allylamine

HCID 746372,2-Diphenylacetyl chloride

HCID 131725417(2S,4EZ)-1-(tert-butoxycarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]imino}-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725453(2S,4EZ)-N-allyl-4-{[(3,4-dichlorobenzyl)oxy]imino}-(diphenylacetyl)-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, diphenylacetyl chloride, and allylamine the title compound was obtained in 54% purity by LC/MS. MS(ESI+): m/z=536.6.

Sources & evidence

ORD record: ord-d23484c940e7480885993b08152714b0
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211601B2

Reaction notes

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