Trifluoroacetic acid → HCID 20025776, compound

HRID 417374Notes

Reaction equation

HRID 417374 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66625110HCID 66625110, compound

Product 1

HCID 20025776HCID 20025776, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Step B A solution of ethyl 2-(4-(tert-butoxycarbonylamino)phenylamino)acetate (772 mg, 2.62 mmol) in dichloromethane (14 mL) was treated with TFA (7 mL)) and the reaction mixture was stirred at 0° C. for 1.5 h. The resulting mixture was concentrated in vacuo and the residue was treated with EtOAc (200 ml) and washed with sat. aqueous Na2CO3, brine, dried over Na2SO4 and concentrated in vacuo to give ethyl 2-(4-aminophenylamino)acetate as a brown oil (483 mg, 94%).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. additionthe residue was treated with EtOAc (200 ml)
  3. washwashed with sat. aqueous Na2CO3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a85c64fa4ceb4a3d97eb8f4c2a134285
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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