Methyl acetoacetate → HCID 86714162, compound

HRID 919979Notes

Reaction equation

HRID 919979 reaction equation
[C:1]1([C@@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][O:11][C:12](=[O:17])[CH2:13][C:14](=O)[CH3:15].[CH3:18][O:19][C:20](=[O:23])[C:21]#[CH:22]>CO>[CH3:18][O:19][C:20](=[O:23])[CH:21]=[CH:22][C:13](=[C:14]([NH:9][C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])[CH3:15])[C:12]([O:11][CH3:10])=[O:17]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 13536Methyl propiolateHCID 758181-Phenethylamine, (-)-

Product 1

HCID 86714162HCID 86714162, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)-1-phenyl-ethylamine (3 g, 24.8 mmol) and 3-oxo-butyric acid methyl ester (3.2 mL, 29.7 mmol) in MeOH (100 mL) was refluxed for 2 h. Propynoic acid methyl ester (3.3 mL, 37.1 mmol) was added, and the resulting mixture was refluxed for 2 days. After cooling to r.t., the solvent was evaporated, and the crude solid was recrystallized from MeOH to give 4.8 g of the title compound as a pale orange solid. MS: (+) m/z 326.29 (M+Na).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturethe resulting mixture was refluxed for 2 days
  3. customthe solvent was evaporated
  4. customthe crude solid was recrystallized from MeOH

Sources & evidence

ORD record
ord-029a78af84d94417b683551570e54c20
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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