Glycolic Acid → HCID 19008605, compound

HRID 1742192Notes

Reaction equation

HRID 1742192 reaction equation
ClCCl.[C:4]([OH:8])(=[O:7])[CH2:5]O.[Cl:9][C:10]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([F:37])[C:11]=1[O:12][C:13]1[CH:28]=[CH:27][C:16]2[N:17]([CH3:26])[C:18](=[O:25])[C:19]([CH3:24])([C:21]([OH:23])=[O:22])[O:20][C:15]=2[CH:14]=1>C(N(CC)CC)C>[Cl:9][C:10]1[CH:32]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:30]=[C:29]([F:37])[C:11]=1[O:12][C:13]1[CH:28]=[CH:27][C:16]2[N:17]([CH3:26])[C:18](=[O:25])[C:19]([CH3:24])([C:21]([O:23][CH2:5][C:4]([OH:8])=[O:7])=[O:22])[O:20][C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 6344DichloromethaneHCID 19008601HCID 19008601, compound2×

Product 1

HCID 19008605HCID 19008605, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a dichloromethane solution (20 ml) of glycolic acid (0.3 g) and triethylamine (1.0 ml) was added an acid chloride (1.5 g) prepared as in Example 6 from 7-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-2,4-dimethyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid (Compound 25), and the mixture was stirred at room temperature for one hour. The reaction mixture was then concentrated under a reduced pressure, the residue was extracted twice with ethyl acetate (20 ml), and the extract was washed with water and then with saturated aqueous sodium chloride, and dried over magnesium sulfate, followed by evaporation of the solvent under a reduced pressure to obtain carboxymethyl 7-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-2,4-dimethyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-2-carboxylate. The acid was dissolved in benzene (20 ml), thionyl chloride (0.9 g) was added thereto, and the mixture was heated under reflux for 3 hours. Then after an evaporation of the solvent under a reduced pressure, the residue was dissolved in dichloromethane (20 ml), ethylamine hydrochloride (0.6 g) and triethylamine (2 ml) were added thereto, and the mixture was stirred for one hour. The reaction mixture was then concentrated under a reduced pressure, and the residue was extracted twice with ethyl acetate (20 ml). The extract was washed with water and then with saturated aqueous sodium chloride, and dried over magnesium sulfate, followed by an evaporation of the solvent under a reduced pressure. The residue was purified by silica gel chromatography (eluant: n-hexane/ethyl acetate=3/1) to give 0.5 g of the title compound (colorless oil).

Workup

  1. concentrationThe reaction mixture was then concentrated under a reduced pressure
  2. extractionthe residue was extracted twice with ethyl acetate (20 ml)
  3. washthe extract was washed with water
  4. dry with materialwith saturated aqueous sodium chloride, and dried over magnesium sulfate
  5. customfollowed by evaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-615f227345854083bfc9a14ff29b5b71
Source dataset
uspto-grants-1994_08
Patent number
US05338719

Reaction notes

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