N,N-Diethylethylenediamine → (2S,4EZ)-4-(tert-butoxyimino)-N-[2-(diethylamino)ethyl]-1-(diphenylacetyl)-2-pyrrolidinecarboxamide

HRID 1745132Notes

Reaction equation

HRID 1745132 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][C@H:9]1[C:19]([OH:21])=O)=[O:7])(C)(C)C.[C:22]1([CH:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)C(Cl)=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH2:38]([N:40]([CH2:44][CH3:45])[CH2:41][CH2:42][NH2:43])[CH3:39]>>[C:15]([O:14][N:13]=[C:11]1[CH2:12][N:8]([C:6](=[O:7])[CH:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C@H:9]([C:19]([NH:43][CH2:42][CH2:41][N:40]([CH2:44][CH3:45])[CH2:38][CH3:39])=[O:21])[CH2:10]1)([CH3:16])([CH3:17])[CH3:18]

Participants

4

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 746372,2-Diphenylacetyl chlorideHCID 131725425(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(tert-butoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725482(2S,4EZ)-4-(tert-butoxyimino)-N-[2-(diethylamino)ethyl]-1-(diphenylacetyl)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(tert-butoxyimino)-2-pyrrolidinecarboxylic acid, diphenylacetyl chloride, and N1,N1-diethyl-1,2-ethanediamine the title compound was obtained in 80% purity by LC/MS. MS(ESI+): m/z=493.4.

Sources & evidence

ORD record
ord-e93262d43e24426f903592694d24e6c6
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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