Tert-Butylamine → (2S)-N-(tert-butyl)-4-methylene-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]-2-pyrrolidinecarboxamide

HRID 1745050Notes

Reaction equation

C(O[C:6]([N:8]1[CH2:15][C:14](=[CH2:16])[CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])(C)(C)C.[O:17]=[C:18]1[C:23](C(Cl)=O)=[CH:22][CH:21]=[C:20]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[O:19]1.[C:32]([NH2:36])([CH3:35])([CH3:34])[CH3:33]>>[C:32]([NH:36][C:10]([C@@H:9]1[CH2:13][C:14](=[CH2:16])[CH2:15][N:8]1[C:6]([C:23]1[C:18](=[O:17])[O:19][C:20]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:21][CH:22]=1)=[O:7])=[O:12])([CH3:35])([CH3:34])[CH3:33]

Participants

Reactant 3

HCID 6385Tert-Butylamine

HCID 21727417(2S)-1-((tert-butoxy)carbonyl)-4-methylidenepyrrolidine-2-carboxylic acid

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

Product 1

HCID 69248629(2S)-N-(tert-butyl)-4-methylene-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from 1-(tert-butoxycarbonyl)-4-methyleneproline, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and tert-butylamine the title compound was obtained in 100% purity by LC/MS. MS(ESI+): m/z=375.4.

Sources & evidence

ORD record: ord-d762c53b71d948d1b6db34ace0b20d84
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07018988B2

Reaction notes

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