2-Methoxyethylamine → (2S,4EZ)-4-(tert-butoxyimino)-N-(2-methoxyethyl)-1-(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl-2-pyrrolidinecarboxamide

HRID 1349045Notes

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][CH2:39][CH2:40][NH2:41]>>[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:41][CH2:40][CH2:39][O:38][CH3:37])=[O:21])[CH2:10]1)([CH3:16])([CH3:17])[CH3:18]

Participants

Reactant 3

HCID 80182-Methoxyethylamine

HCID 222235122-oxo-6-pentyl-2H-pyran-3-carbonyl chloride

HCID 131725425(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(tert-butoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725428(2S,4EZ)-4-(tert-butoxyimino)-N-(2-methoxyethyl)-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 2-methoxyethylamine the title compound was obtained in 75% purity by LC/MS. MS(ESI+): m/z=450.2.

Sources & evidence

ORD record: ord-6450d76f17984a84a8a3542aa04d0afa
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211601B2

Reaction notes

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