3-Amino-9-ethylcarbazole → (2S,4EZ)-4(ethoxyimino)-N-(9-ethyl-9H-carbazol-3-yl)-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]-2-pyrrolidinecarboxamide

HRID 1349137Notes

Reaction equation

HRID 1349137 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]=[C:21]1[C:26](C(Cl)=O)=[CH:25][CH:24]=[C:23]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[O:22]1.[CH2:35]([N:37]1[C:49]2[CH:48]=[CH:47][C:46]([NH2:50])=[CH:45][C:44]=2[C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH3:36]>>[CH2:15]([O:14][N:13]=[C:11]1[CH2:12][N:8]([C:6]([C:26]2[C:21](=[O:20])[O:22][C:23]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:24][CH:25]=2)=[O:7])[C@H:9]([C:17]([NH:50][C:46]2[CH:47]=[CH:48][C:49]3[N:37]([CH2:35][CH3:36])[C:38]4[C:43]([C:44]=3[CH:45]=2)=[CH:42][CH:41]=[CH:40][CH:39]=4)=[O:19])[CH2:10]1)[CH3:16]

Participants

4

Reactant 3

HCID 85883-Amino-9-ethylcarbazoleHCID 222235122-oxo-6-pentyl-2H-pyran-3-carbonyl chlorideHCID 58714540(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(ethoxyirnino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725492(2S,4EZ)-4(ethoxyimino)-N-(9-ethyl-9H-carbazol-3-yl)-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(ethoxyimino)-2-pyrrolidinecarboxylic acid, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and 9-ethyl-9H-carbazol-3-amine the title compound was obtained in 75% purity by LC/MS. MS(ESI+): m/z=557.4.

Sources & evidence

ORD record
ord-8e8d9dc40fbe44f8a6e8bb8cbf7fc84e
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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