Cyclopropylamine → HCID 19767055, compound

HRID 1590514Notes

Reaction equation

HRID 1590514 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5]([NH:9][C:10]([C:12]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:21](OC)=[O:22])[O:14][N:13]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>CO.C(OC)(C)(C)C>[C:5]([NH:9][C:10]([C:12]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:21]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:22])[O:14][N:13]=1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 19767053HCID 19767053, compound

Product 1

HCID 19767055HCID 19767055, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

0.75 g (I3.1 mmol) of cyclopropylamine was added dropwise at 20° C., with cooling, to a solution of 2.5 g (8.8 mmol) of dimethyl 3-tert-butylaminocarbonylisoxazole-4,5-dicarboxylate in 50 ml of dry methanol, and the mixture was stirred at room temperature for 20 hours. The solvents were stripped off under reduced pressure, and the residue was taken up in methyl tert-butyl ether and extracted with dilute HCl and once with water. The organic phase was then dried over magnesium sulfate, and the solution was evaporated. The resulting methyl3-tert-butylaminocarbonyl-5-cyclopropylaminocarbonylisoxazole-4-carboxylate was purified by column chromatography (SiO2 ; cyclohexane/ethyl acetate 4:1).

Workup

  1. extractionextracted with dilute HCl and once with water
  2. dry with materialThe organic phase was then dried over magnesium sulfate
  3. customthe solution was evaporated
  4. customThe resulting methyl3-tert-butylaminocarbonyl-5-cyclopropylaminocarbonylisoxazole-4-carboxylate was purified by column chromatography (SiO2 ; cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-8b4a58815b0141a089f338be9197a0f8
Source dataset
uspto-grants-1993_04
Patent number
US05203907

Reaction notes

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