Hydrochloric Acid → 2-Amino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl ester

HRID 491762Notes

Reaction equation

HRID 491762 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]([NH:15]C(OC(C)(C)C)=O)([CH3:14])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.Cl.[OH-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:23])[C:4]([NH2:15])([CH3:14])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 576789232-tert-Butoxycarbonylamino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl ester

Product 1

HCID 576789242-Amino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl esterYield 46.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-tert-butoxycarbonylamino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl ester (954 mg, 2.92 mmol) in methanol (10 mL) was added HCl (3 mL, 12 N). The mixture was heated to 55° C. until the MS indicated no starting material remained. After cooling to ambient temperature, the solution was treated with aqueous NaOH (40 mL, 1N) and extracted several times with DCM. The combined extracts were concentrated and purified by flash chromatography (SiO2, 5% MeOH/DCM) to yield the title compound as a yellow oil (305 mg, 46%).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted several times with DCM
  3. concentrationThe combined extracts were concentrated
  4. custompurified by flash chromatography (SiO2, 5% MeOH/DCM)

Sources & evidence

ORD record
ord-b34f77d62bfc48b7936fccf1afae8378
Source dataset
uspto-grants-2009_05
Patent number
US07531565B2

Reaction notes

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