Ammonium Hydroxide → HCID 46892231, compound

HRID 72322Notes

Reaction equation

HRID 72322 reaction equation
[CH2:1]([NH: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.C1N=C[N:24]([C:27](N2C=NC=C2)=[O:28])C=1.[OH-].[NH4+]>C1COCC1>[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][O:21][C:27](=[O:28])[NH2:24])[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 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 66617661HCID 66617661, compound

Product 1

HCID 46892231HCID 46892231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[3-(4-benzylamino-phenyl)-isoxazol-5-yl]-methanol (178 mg, 0.63 mmol) was dissolved in THF (20 ml, 0.03 M), to which was added CDI (154 mg, 0.95 mmol). After the mixture was stirred at room temperature for about 1 hour, 1 ml of ammonium hydroxide was added and the resulting mixture was stirred for another 3 hours. The completion of the reaction was confirmed by liquid chromatography, and the THF was distilled under reduced pressure to obtain a pale yellow solid compound. The solid compound was extracted three times with water and ethyl acetate, the organic solvent layer was dried under reduced pressure, and then a crude compound was purified by column chromatography on silica gel using ethyl acetate/hexane (1:3) to obtain carbamic acid 3-(4-benzylamino-phenyl)-isoxazol-5-ylmethyl ester as a white solid.

Workup

  1. stirringthe resulting mixture was stirred for another 3 hours
  2. distillationthe THF was distilled under reduced pressure
  3. customto obtain a pale yellow solid compound
  4. extractionThe solid compound was extracted three times with water and ethyl acetate
  5. customthe organic solvent layer was dried under reduced pressure
  6. customa crude compound was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ad1c76eb58054d6b8f86366a88740455
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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