Hydrochloric Acid → 2-((4-Chlorophenyl)formamido)propanoic acid

HRID 1799797Notes

Reaction equation

HRID 1799797 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[OH-].[K+].[Cl:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1.Cl>O>[Cl:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH:1][CH:2]([CH3:3])[C:4]([OH:6])=[O:5])=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 85014-Chlorobenzoyl chlorideHCID 14797Potassium Hydroxide

Product 1

HCID 27287552-((4-Chlorophenyl)formamido)propanoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of L-Alanine (2.67 g, 30.0 mmol) and KOH (3.90 g, 69.5 mmol) in water (50.0 mL) was added 4-chlorobenzoyl chloride (5.25 g, 30.0 mmol). After stirring at RT for 16H, the reaction mixture was cooled to 0° C., acidified to pH=2 with 10 M HCl and extracted with EtOAc (3×75 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, concentrated and air dried under vacuum to afford 5.80 g (85% yield) of the title compound as a white solid that was carried forward without further purification: 1H NMR (500 MHz, DMSO-d6) δ 12.62 (1H, br. s.), 8.76 (1H, d, J=7.15 Hz), 7.90 (2H, d, J=8.25 Hz), 7.55 (2H, d, J=8.25 Hz), 4.40 (1H, qd, J=7.33, 7.15 Hz), 1.38 (3H, d, J=7.15 Hz); HPLC retention time: 2.223 min; LCMS (ES): m/z 228 [M+H]+.

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. extractionextracted with EtOAc (3×75 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customair dried under vacuum

Sources & evidence

ORD record
ord-814e2e244c414499b260acb74d374526
Source dataset
uspto-grants-2013_01
Patent number
US08344160B2

Reaction notes

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