Methanol → HCID 18331431, compound

HRID 1297183Notes

Reaction equation

HRID 1297183 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([N:25]=[C:26]=[S:27])(=O)C1C=CC=CC=1.CO.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:26]([NH2:25])=[S:27])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 10775412tert-butyl N-((3-aminophenyl)methyl)carbamate

Product 1

HCID 18331431HCID 18331431, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3 g (13.5 mmol) (3-amino-benzyl)-carbamic acid tert-butyl ester (WO 9740028 A1) and 1.81 ml (13.5 mmol) benzoyl isothiocyanate in 60 ml THF was stirred at room temperature for 1 h and afterwards evaporated under reduced pressure. 80 ml MeOH and 5.6 g (40.5 mmol) potassium carbonate in 80 ml water were added and the mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure and extracted with ethyl acetate. The organic layers were washed with saturated NaHCO3 solution and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica eluting with a gradient of hexane/ethyl acetate to yield after evaporation of the product fractions 3.56 g (94%) of the title compound as yellow amorphous solid.

Workup

  1. customafterwards evaporated under reduced pressure
  2. stirringthe mixture was stirred at room temperature for 16 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe organic layers were washed with saturated NaHCO3 solution
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica eluting with a gradient of hexane/ethyl acetate
  8. customto yield
  9. customafter evaporation of the product fractions 3.56 g (94%) of the title compound as yellow amorphous solid

Sources & evidence

ORD record
ord-8b26e2a124a3460faba67fb510c3ecc4
Source dataset
uspto-grants-2007_07
Patent number
US07250431B2

Reaction notes

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