Water → 2-[(4-Methylphenyl)amino]acetic acid

HRID 2115328Notes

Reaction equation

HRID 2115328 reaction equation
C([O:5][C:6](=[O:16])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[C:12]1([CH3:15])[CH:13]=[CH:14][C:9]([NH:8][CH2:7][C:6]([OH:16])=[O:5])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 13599134Tert-butyl 2-[(4-methylphenyl)amino]acetate

Product 1

HCID 2422362-[(4-Methylphenyl)amino]acetic acidYield 54.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude p-tolylamino-acetic acid tert-butyl ester (200 mmol) in DCM (600 mL) was cooled to 0° C. and treated with TFA (150 mL). The reaction mixture was allowed to reach RT and stirred for 4 d. Water (200 mL) was added, the layers were separated and the aqueous layer was extracted with DCM (4×200 mL). The aqueous layer was adjusted to pH 8 by addition of saturated NaHCO3 solution and extracted with ethyl acetate (4×200 mL). The combined organic layers were dried with Na2SO4 and the solvents were removed in vacuo to give the crude acid (18 g) which was used in the next step without further purification.

Workup

  1. customto reach RT
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with DCM (4×200 mL)
  4. additionThe aqueous layer was adjusted to pH 8 by addition of saturated NaHCO3 solution
  5. extractionextracted with ethyl acetate (4×200 mL)
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-b0a404f133b446bb8a08b239d4b23097
Source dataset
uspto-grants-2008_10
Patent number
US07435815B2

Reaction notes

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