Hydrochloric Acid → HCID 68458255, compound

HRID 498926Notes

Reaction equation

HRID 498926 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])=[CH:13][C:3]=1[C:4]([O:6][C@@H:7]([CH3:12])[C:8]([O:10]C)=[O:9])=[O:5].Cl>C(O)(=O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[N:19]([CH3:28])[C:18]2=[O:29])=[CH:13][C:3]=1[C:4]([O:6][C@@H:7]([CH3:12])[C:8]([OH:10])=[O:9])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69533135HCID 69533135, compound

Product 1

HCID 68458255HCID 68458255, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7.0 g (16 mmol) of methyl (S)-2-[2-chloro-5-(3-methyl-2,6-di-oxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyl-oxy]propionate from example 3.1 were dissolved in 50 ml of acetic acid, 50 ml of conc. hydrochloric acid were added and the solution was heated under reflux for 4 hours. Most of the acetic acid was distilled off, and the solution that remained was poured onto ice-water. The aqueous phase was extracted three times with ethyl acetate, the organic phase was dried over sodium sulfate, the drying agent was filtered off and the filtrate was concentrated to dryness, which gave 5.7 g of (S)-2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]propionic acid.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 4 hours
  3. distillationMost of the acetic acid was distilled off
  4. additionthe solution that remained was poured onto ice-water
  5. extractionThe aqueous phase was extracted three times with ethyl acetate
  6. dry with materialthe organic phase was dried over sodium sulfate
  7. filtrationthe drying agent was filtered off
  8. concentrationthe filtrate was concentrated to dryness, which

Sources & evidence

ORD record
ord-7969841753f644d3907ea628688218f9
Source dataset
uspto-grants-2010_08
Patent number
US07767624B2

Reaction notes

Loading…