3-Amino-9-ethylcarbazole → (2S,4EZ)-4-(ethoxyimino)-N-(9-ethyl-9H-carbazol-3-yl)-1-(-phenoxyacetyl)-2-pyrrolidinecarboxamide

HRID 1349016Notes

Reaction equation

HRID 1349016 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH2:15][CH3:16])[CH2:10][C@H:9]1[C:17]([OH:19])=O)=[O:7])(C)(C)C.[O:20]([CH2:27]C(O)=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:31]([N:33]1[C:45]2[CH:44]=[CH:43][C:42]([NH2:46])=[CH:41][C:40]=2[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH3:32]>>[CH2:15]([O:14][N:13]=[C:11]1[CH2:12][N:8]([C:6](=[O:7])[CH2:27][O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:9]([C:17]([NH:46][C:42]2[CH:43]=[CH:44][C:45]3[N:33]([CH2:31][CH3:32])[C:34]4[C:39]([C:40]=3[CH:41]=2)=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:19])[CH2:10]1)[CH3:16]

Participants

4

Reactant 3

HCID 85883-Amino-9-ethylcarbazoleHCID 19188Phenoxyacetic AcidHCID 58714540(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(ethoxyirnino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725399(2S,4EZ)-4-(ethoxyimino)-N-(9-ethyl-9H-carbazol-3-yl)-1-(-phenoxyacetyl)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 2, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(ethoxyimino)-2-pyrrolidinecarboxylic acid, phenoxyacetic acid, and 9-ethyl-9H-carbazol-3-amine the title compound was obtained after column chromatography as an off-white solid as a mixture of E/Z-isomers. The isomers were then separated using column chromatography.

Sources & evidence

ORD record
ord-78406ca977ca4cfb90cf1203bd234b70
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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