Methylamine → Methyl-carbamic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester

HRID 72327Notes

Reaction equation

HRID 72327 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][OH:21])[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](N1C=CN=C1)([N:24]1C=CN=[CH:25]1)=[O:23].CN>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][O:21][C:22](=[O:23])[NH:24][CH3:25])[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 64164588[3-(4-Benzyloxy-phenyl)-isoxazol-5-yl]-methanol

Product 1

HCID 46893645Methyl-carbamic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 g of the compound [3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methanol in Example 1 was dissolved in 10 ml of THF, to which solution was added 0.49 g (1.7 equivalents) of 1,1′-carbonyldiimidazole. The consumption of all the reactants was confirmed by TLC, and 2 equivalents of methyl amine were added to the reaction solution. 2 hours later, the solvent was distilled off under reduced pressure, 50 ml of a 1N—HCl aqueous solution was placed in the reactants, and the mixture was extracted three times with 30 ml of ethyl acetate. An obtained organic layer was distilled under reduced pressure, followed by column chromatography to obtain methyl-carbamic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester as a desired compound.

Workup

  1. customThe consumption of all the reactants
  2. additionwere added to the reaction solution
  3. distillation2 hours later, the solvent was distilled off under reduced pressure, 50 ml of a 1N—HCl aqueous solution
  4. extractionthe mixture was extracted three times with 30 ml of ethyl acetate
  5. distillationAn obtained organic layer was distilled under reduced pressure

Sources & evidence

ORD record
ord-b1a11c10771c4d3a82df0946e8ad9b6e
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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