Ethyl propiolate → HCID 59252551, compound

HRID 237880Notes

Reaction equation

HRID 237880 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[O:14][C:13]([NH2:15])=[N:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](OCC)(=[O:19])[C:17]#[CH:18]>C(O)C>[CH2:1]([O:8][CH2:9][C@H:10]1[O:14][C:13]2=[N:15][C:16](=[O:19])[CH:17]=[CH:18][N:12]2[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 68527184HCID 68527184, compound

Product 1

HCID 59252551HCID 59252551, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-5-(benzyloxymethyl)-(4,5-dihydro-oxazol-2-yl)amine (6.02 g, 29.4 mmol) in ethanol (210 mL) was added ethyl propiolate (2.97 mL, 29.4 mmol). The reaction mixture was stirred at reflux for 2.5 hours. The mixture was cooled to room temperature, concentrated under vacuum and purified by column chromatography on silica gel (4:1 ethyl acetate:heptanes to 10% methanol in dichloromethane) to provide 2.09 g (28%) of the title compound. [α]D25 −30.09 (c 0.545, CHCl3).

Workup

  1. temperatureat reflux for 2.5 hours
  2. concentrationconcentrated under vacuum
  3. custompurified by column chromatography on silica gel (4:1 ethyl acetate:heptanes to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f0d25380bac74508a869e2fb12d63d08
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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