Ethyl propiolate → HCID 131731179, compound

HRID 237878Notes

Reaction equation

HRID 237878 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:15])([CH3:14])[C@H:8]1[O:12][C:11]([NH2:13])=[N:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:16](OCC)(=[O:19])[C:17]#[CH:18]>C(O)C>[C:1]([SiH2:5][O:6][C:7]([CH3:15])([CH3:14])[C@H:8]1[O:12][C:11]2=[N:13][C:16](=[O:19])[CH:17]=[CH:18][N:10]2[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 131731180HCID 131731180, compound

Product 1

HCID 131731179HCID 131731179, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-oxazol-2-ylamine (6.65 g, 28.9 mmol) in ethanol (150 mL) was added ethyl propiolate (2.92 mL, 28.9 mmol). The reaction mixture was stirred at reflux for 2 hours. The mixture was cooled to room temperature, concentrated under vacuum and purified by column chromatography on silica gel (0-10% methanol in dichloromethane). This afforded 2.45 g (30%) of the title compound.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrated under vacuum
  3. custompurified by column chromatography on silica gel (0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8fcc923e5e4c43fc8f2870725cd728ac
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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