Hydrochloric Acid → HCID 86666266, compound

HRID 1026213Notes

Reaction equation

HRID 1026213 reaction equation
[OH-:1].[Na+].[C:3]([NH:6][C@@H:7]([CH3:20])[CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:13](C(OC)=O)=[CH:12][CH:11]=1)(=[O:5])[CH3:4].Cl.[CH3:22][OH:23]>>[C:3]([NH:6][C@@H:7]([CH3:20])[CH2:8][O:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:18][C:19]=1[C:22]([OH:23])=[O:1])(=[O:5])[CH3:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67777625HCID 67777625, compound

Product 1

HCID 86666266HCID 86666266, compound

Conditions

Temperature
60 °C

Procedure

1M Aqueous sodium hydroxide solution (23 mL) was added to a solution (7 mL) of methyl 4-{[(2S)-2-(acetylamino)propyl]oxy}benzoate (3.80 g) in methanol, and the mixture was stirred at 60° C. for 40 min. The reaction mixture was neutralized with 6M hydrochloric acid, and extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with diisopropyl ether, and the precipitated solid was collected by filtration to give the title compound (3.33 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe residue was washed with diisopropyl ether
  6. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-488b97974ec0498e8b6fece336d234a6
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

Loading…