HCID 67461269, compound → HCID 67467972, compound

HRID 1619996Notes

Reaction equation

HRID 1619996 reaction equation
[CH:1]1([CH:4]([C:13]([N:15]2[CH2:20][CH2:19][C:18]3[N:21]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:23][C:17]=3[CH2:16]2)=[O:14])[CH2:5][C:6]([O:8][C:9](C)(C)C)=[O:7])[CH2:3][CH2:2]1>Cl>[CH:1]1([CH:4]([C:13]([N:15]2[CH2:20][CH2:19][C:18]3[N:21]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:23][C:17]=3[CH2:16]2)=[O:14])[CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 67461269HCID 67461269, compound

Product 1

HCID 67467972HCID 67467972, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

1.4 g (3.6 mmol) tert-butyl 3-cyclopropyl-4-(2-phenyl-6,7-dihydro-4H-oxazolo[5,4-c]pyridin-5-yl)-4-oxobutanoate are mixed with 150 ml of 1.25 M HCl and stirred for 8 h at 60° C. The mixture is evaporated down and the residue is taken up in dichloromethane. It is filtered to remove the precipitate and the filtrate is evaporated down. This yields 650 mg of colourless resin which is dissolved in 10 ml MeOH and combined with 1 ml 2M trimethylsilyl-diazomethane solution in hexane while being cooled to −5° C. The yellow solution is left overnight with stirring while the ice bath is heated. The solvent is eliminated and the residue is reacted in the following step without any further purification.

Workup

  1. customThe mixture is evaporated down
  2. filtrationIt is filtered
  3. customto remove the precipitate
  4. customthe filtrate is evaporated down
  5. dissolutionThis yields 650 mg of colourless resin which is dissolved in 10 ml MeOH
  6. temperaturewhile being cooled to −5° C
  7. waitThe yellow solution is left overnight
  8. stirringwith stirring while the ice bath
  9. temperatureis heated
  10. customthe residue is reacted in the following step without any further purification

Sources & evidence

ORD record
ord-3da38e46fbc84490aa26de605d70ef0d
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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