Hydrochloric Acid → (4-Fluoro-benzylamino)-phenyl-acetic acid hydrochloride

HRID 77008

Reaction equation

HRID 77008 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][CH:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12]([OH:14])=[O:13].[OH-].[Na+].[BH4-].[Na+].[ClH:25]>CO.O1CCOCC1>[ClH:25].[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:10][CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 38662-PhenylglycineHCID 14798Sodium HydroxideHCID 680234-FluorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 67425426(4-Fluoro-benzylamino)-phenyl-acetic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Fluorobenzaldehyde (0.25 mL, 2.38 mmol), 2-amino-2-phenylacetic acid (300 mg, 1.98 mmol) and NaOH (79 mg, 1.98 mmol) are dissolved in MeOH (20 mL) and stirred at RT overnight. The reaction is cooled at 0° C. and NaBH4 (150 mg, 3.97 mmol) is added. After being stirred at 0° C. for 30 minutes, the reaction is judged complete by UPLC-MS analysis. 4M HCl in dioxane is added dropwise till pH 5 and the precipitate is collected by suction filtration, washed with Et2O and dried under vacuum at 40° C. to obtain intermediate I129 as a white solid (587 mg, quantitative yield).

Workup

  1. temperatureThe reaction is cooled at 0° C.
  2. stirringAfter being stirred at 0° C. for 30 minutes
  3. filtrationthe precipitate is collected by suction filtration
  4. washwashed with Et2O
  5. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-f545af928ca34d60ae9e8a8e446c8507
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Linked notes

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