Hydrochloric Acid → ((3-(Trifluoromethyl)benzoyl)amino)acetic acid

HRID 2036179Notes

Reaction equation

HRID 2036179 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[F:8][C:9]([F:20])([F:19])[C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](Cl)=[O:14].Cl>C(#N)C>[F:8][C:9]([F:19])([F:20])[C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 14798Sodium HydroxideHCID 752573-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 2777432((3-(Trifluoromethyl)benzoyl)amino)acetic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
1.5 °C

Procedure

Glycine 0.763 g (10.16 mmol) was suspended into acetonitrile 20 ml and 2M NaOH aqueous solution 12.7 ml (25.40 mmol, 2.5 eq.) was also added. After chilling at 0-3° C., 2.12 g (10.16 mmol, 1.0 eq.) of 3-(trifluoromethyl)-benzoyl chloride was diluted with 4 ml acetonitrile and was added dropwise slowly to reaction mixture. After one hour agitation at same temperature, pH was controlled to 2 to 3 with 3N hydrochloric acid aqueous solution. After keeping upright at room temperature, upper organic solution was separated, and lower aqueous solution was extracted with ethylacetate three times. Those organic solution obtained as above was brought all together, dried with anhydrous magnesium sulfate and concentrated removing its solvent under decompression. Residues was solidified with tolene, filtered, washed with normal hexane and 2.28 g (91%) target compound as white solid was yielded.

Workup

  1. additionwas also added
  2. additionwas added dropwise slowly to reaction mixture
  3. customAfter keeping upright at room temperature
  4. customupper organic solution was separated
  5. extractionlower aqueous solution was extracted with ethylacetate three times
  6. customThose organic solution obtained as
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customremoving its solvent under decompression
  10. filtrationfiltered
  11. washwashed with normal hexane
  12. custom2.28 g (91%) target compound as white solid was yielded

Sources & evidence

ORD record
ord-41ba3d44c869431da979f720ab866056
Source dataset
uspto-grants-2013_11
Patent number
US08575173B2

Reaction notes

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