Ammonia → HCID 54707528, compound

HRID 524063Notes

Reaction equation

HRID 524063 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

5

Reactant 3

HCID 222AmmoniaHCID 31214Ethyl orthoformateHCID 10921903Diethyl 2-methyl-3-oxopentanedioate

Product 1

HCID 54707528HCID 54707528, compound

Reagents, catalysts & solvents 1

HCID 54291718HCID 54291718, compoundSolvent

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

  1. filtrationThe precipitate was collected via filtration
  2. dissolutiondissolved in dichloromethane (400 mL)
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1eba5f04415647319e4d4c52b1c8b9d0
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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