Acetic Acid → 92912-20-4

HRID 2069008Notes

Reaction equation

HRID 2069008 reaction equation
[CH2:1]([N:8]([CH2:18][C:19]([O:21]CC)=O)[C:9](=[O:17])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[Na].C(O)(=O)C>O1CCOCC1.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:18][C:19]([OH:21])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 5360545Sodium2×HCID 13300084HCID 13300084, compound

Product 1

HCID 5957576992912-20-4Yield 40%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Ethyl 4-(benzyl(2-ethoxy-2-oxoethyl)amino)-4-oxobutanoate (123.2 g, 0.4 mol) in ethanol (37 g, 0.8 mol) and dioxane (200 ml) was added dropwise to a suspension of sodium (18.4 g, 0.8 mol) in dioxane (500 mL). The resulting mixture was heated at reflux until the sodium metal was no longer visible. After cooling the mixture to ambient temperature, acetic acid (48 g, 0.8 mol) was added. Standard extractive workup with ethyl acetate, gave a crude product that was purified by re-crystallization from ether/acetone to afford the title product as a yellow solid (40 g; yield=40%). 1H NMR (300 MHz, CD3OD) δ: 11.81 (s, 1H), 7.19-7.41 (m, 5H), 4.65 (s, 2H), 4.25 (q, J=7.2 Hz, 2H), 3.91 (t, J=3 Hz, 2H), 3.27 (t, J=3 Hz, 2H), 1.32 (t, J=7.2 Hz, 3H). LC-MS: m/z=276 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. customwas purified by re-crystallization from ether/acetone

Sources & evidence

ORD record
ord-1178fb31987d40e0b35513a292453113
Source dataset
uspto-grants-2012_10
Patent number
US08299084B2

Reaction notes

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