3-Cyclopropyl-3-Oxopropionic Acid Methyl Ester → HCID 67984108, compound

HRID 1748161Notes

Reaction equation

HRID 1748161 reaction equation
[CH:1]1([C:4](=[O:10])[CH2:5][C:6]([O:8]C)=[O:7])[CH2:3][CH2:2]1.C[O-].[Na+].O[N:15]=[C:16](Cl)[C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[CH:1]1([C:4]2[O:10][N:15]=[C:16]([CH:17]3[CH2:19][CH:18]3[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:5]=2[C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl EsterHCID 10942334Sodium MethoxideHCID 86704400HCID 86704400, compound

Product 1

HCID 67984108HCID 67984108, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of methyl 3-cyclopropyl-3-oxopropanoate (0.36 mL, 2.9 mmol) in methanol (8 mL) was cooled to 0°C. and treated with sodium methoxide (0.76 mL of a 25% wt. solution in MeOH). After stirring fo(20 minutes, trans-N-hydroxy-2-phenylcyclopropanecarbimidoyl chloride rac-I-6D (0.57 g, 2.9 mmol) in methanol (0.5 mL) was added dropwise. The reaction mixture was warmed to rt and stirred fo(1 h. The reaction was concentrated in vacuo, diluted with water and extracted with dichloromethane. The aqueous was acidified with 6N HCl to pH=5 and extracted again with dichloromethane. The organics were washed with brine dried over Na2SO4, filtered, concentrated to yield 5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazole-4-carboxylic acid as clear oil which was directly used in the next step without further purification. MS m/z 270.1 (M+1).

Workup

  1. additionwas added dropwise
  2. stirringstirred
  3. custom1 h
  4. concentrationThe reaction was concentrated in vacuo
  5. additiondiluted with water
  6. extractionextracted with dichloromethane
  7. extractionextracted again with dichloromethane
  8. washThe organics were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-3dd8879a6312418eaec64b92f7a0fe63
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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