Ammonia → HCID 54707528, compound

HRID 2274207Notes

Reaction equation

[CH3:1][CH:2]([C:8](=[O:15])[CH2:9][C:10](OCC)=O)[C:3](OCC)=[O:4].C(O[CH:19]([O:23]CC)[O:20][CH2:21][CH3:22])C.[NH3:26]>O(C(=O)CC)OOC(=O)CC>[OH:15][C:8]1[C:9]([C:19]([O:20][CH2:21][CH3:22])=[O:23])=[CH:10][NH:26][C:3](=[O:4])[C:2]=1[CH3:1]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of diethyl 2-methyl-3-oxopentanedioate (10 g, 46.25 mmol) in 1,1′-trioxidanediyldipropan-1-one (400 mL) was added triethoxymethane (38 mL, 231.25 mmol), and the mixture was heated at 120° C. for 4 h, followed by the addition of 30% ammonia (600 mL) at 0° C. The reaction mixture was stirred at RT for another 2 h. LCMS monitored the reaction was completed. The precipitate was collected via filtration and dissolved in dichloromethane (400 mL). The solid was filtered off, and the filtrate was concentrated to get the title compound (5.5 g, crude) as a yellow solid. MS (ES+) C9H11NO4 requires: 197. Found: 198 [M+H]+.

Workup

filtrationThe precipitate was collected via filtration
dissolutiondissolved in dichloromethane (400 mL)
filtrationThe solid was filtered off
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-57df84b581694bac8f01eca4d851dcbb
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126951B2

Reaction notes

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