Hydrochloric Acid → HCID 69672259, compound

HRID 1751509Notes

Reaction equation

HRID 1751509 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl[C:16]([O:18][CH3:19])=[O:17].Cl>C1COCC1>[F:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:2]([NH:1][C:16]([O:18][CH3:19])=[O:17])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 5800732-Fluoro-DL-phenylglycine

Product 1

HCID 69672259HCID 69672259, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Amino-(2-fluoro-phenyl)-acetic acid (0.5 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 methyl 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 (2-Fluoro-phenyl)-methoxycarbonylamino-acetic acid as an off-white solid. LCMS-ESI+: calc'd for C10H10FNO4: 227.06 (M+); Found: 228.17 (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-381717c1772d4b91b94876e9a76d61db
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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