Hydrochloric Acid → HCID 22665825, compound

HRID 1751507Notes

Reaction equation

HRID 1751507 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl[C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16].Cl>C1COCC1>[CH:18]([O:17][C:15]([NH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4])=[O:16])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 38662-PhenylglycineHCID 7917Isopropyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 22665825HCID 22665825, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Amino-phenyl-acetic acid (0.505 g, 2.44 mmol) was dissolved in THF (7 mL) and cooled to 0° C. in an external ice/brine bath. Aqueous sodium hydroxide (12.5M, 0.47 mL, 5.856 mmol) and isopropyl chloroformate (0.23 mL, 2.948 mmol) were added at 0° C. Upon completion of the addition, the solution was removed from the ice bath and allowed to warm to room temperature, and stirred. After 18 hours, the crude reaction mixture was adjusted to pH 1 with 1N HCl and extracted twice with diethyl ether. The combined organic layers were washed with brine, dried with magnesium sulfate and concentrated to give Isopropoxycarbonylamino-phenyl-acetic acid as an off-white solid. LCMS-ESI+: calc'd for C12H15NO4: 237.10 (M+); Found: 238.05 (M+H+).

Workup

  1. additionUpon completion of the addition
  2. customthe solution was removed from the ice bath
  3. temperatureto warm to room temperature
  4. customthe crude reaction mixture
  5. extractionextracted twice with diethyl ether
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dd5ac77c30c3428ba207ec445d65c818
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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