Formic Acid → [Oxazol-2-yl-(toluene-4-sulfonyl)-methyl]-carbamic Acid Tert-Butyl Ester

HRID 34103

Reaction equation

HRID 34103 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.[C:8](=[O:15])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[NH2:9].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([O-])(=[O:24])=[O:23])=[CH:18][CH:17]=1.[Na+].C(O)=O>CO.O>[C:11]([O:10][C:8](=[O:15])[NH:9][CH:6]([C:2]1[O:1][CH:5]=[CH:4][N:3]=1)[S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 77922tert-Butyl carbamateHCID 3720192Sodium 4-methylbenzenesulfonateHCID 147866091,3-Oxazole-2-carboxaldehyde

Product 1

HCID 60034835[Oxazol-2-yl-(toluene-4-sulfonyl)-methyl]-carbamic Acid Tert-Butyl EsterYield 24.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

300 mg of oxazole 2-carboaldehyde was dissolved in a mixed solvent of 3 mL of methanol and 6 mL of water, added successively with 363 mg of tert-butyl carbamate, 552 mg of sodium p-toluenesulfonate and 0.76 mL of formic acid and stirred at room temperature for 16 hours and 30 minutes. The precipitated crystals were collected by filtration, washed with water, and dried under reduced pressure, to afford 247 mg of the title compound as colorless crystals.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-3b7aa62a381549e18666f9b8cf1832d0
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

Loading…