Dimethylformamide dimethyl acetal → (Z)-N-(2-adamantyl)-2-(cyclopentanecarbonyl)-3-dimethylamino-prop-2-enamide

HRID 1799419Notes

Reaction equation

CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH:10]1[NH:19][C:20](=[O:29])[CH2:21][C:22]([CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23])[CH2:16]2>O1CCOCC1>[CH:9]12[CH2:16][CH:15]3[CH2:14][CH:13]([CH2:12][CH:11]([CH2:17]3)[CH:10]1[NH:19][C:20](=[O:29])/[C:21](/[C:22]([CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23])=[CH:3]\[N:4]([CH3:5])[CH3:6])[CH2:18]2

Participants

Conditions

Temperature: 100 °C

Procedure

N,N-Dimethylformamide dimethyl acetal (0.587 mL, 4.42 mmol) was added to N-(2-adamantyl)-3-cyclopentyl-3-oxo-propanamide (Intermediate #72), (1.023 g, 3.53 mmol) in 1,4-dioxane (25 mL). The resulting solution was stirred at 100° C. for 2 hours. The resulting mixture was evaporated to dryness to afford (Z)—N-(2-adamantyl)-2-(cyclopentanecarbonyl)-3-dimethylamino-prop-2-enamide (1.210 g, 99%).

Workup

customThe resulting mixture was evaporated to dryness

Sources & evidence

ORD record: ord-ec1debc13bd1468eb62305e2bf2c6193
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344016B2

Reaction notes

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