Veratrylamine → (2S,4EZ)-4-(tert-butoxyimino)-N-(3,4-dimethoxybenzyl)-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]-2-pyrrolidinecarboxamide

HRID 1349178Notes

Reaction equation

HRID 1349178 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.[O:22]=[C:23]1[C:28](C(Cl)=O)=[CH:27][CH:26]=[C:25]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[O:24]1.[CH3:37][O:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[O:47][CH3:48])[CH2:42][NH2:43]>>[C:15]([O:14][N:13]=[C:11]1[CH2:12][N:8]([C:6]([C:28]2[C:23](=[O:22])[O:24][C:25]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:26][CH:27]=2)=[O:7])[C@H:9]([C:19]([NH:43][CH2:42][C:41]2[CH:44]=[CH:45][C:46]([O:47][CH3:48])=[C:39]([O:38][CH3:37])[CH:40]=2)=[O:21])[CH2:10]1)([CH3:16])([CH3:17])[CH3:18]

Participants

4

Reactant 3

HCID 79832VeratrylamineHCID 222235122-oxo-6-pentyl-2H-pyran-3-carbonyl chlorideHCID 131725425(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(tert-butoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131726376(2S,4EZ)-4-(tert-butoxyimino)-N-(3,4-dimethoxybenzyl)-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-(tert-butoxyimino)-2-pyrrolidinecarboxylic acid, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and 3,4-dimethoxybenzylamine the title compound was obtained in 63% purity by LC/MS. MS(ESI+): m/z=542.4.

Sources & evidence

ORD record
ord-df18a029300944f28f31b5f43c325442
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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