Trifluoroacetic acid → HCID 22060556, compound

HRID 1430622Notes

Reaction equation

HRID 1430622 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15]C(OC(C)(C)C)=O)[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:23])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59363840HCID 59363840, compound

Product 1

HCID 22060556HCID 22060556, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3-tert-Butoxycarbonylamino-phenoxy)-2-methyl-propionic acid ethyl ester (0.8 g, 2.4 mmol) in DCM (10 ml) at 0° C. was added TFA (10 ml) and stirred at 0° C. for 100 min. The solvent was removed under reduced pressure; residue was dissolved in DCM and treated with 2.5M solution of NaOH. The organic layer was separated and dried over Na2SO4, concentrated to yield 2-(3-amino-phenoxy)-2-methyl-propionic acid ethyl ester (0.5 g, mmol, 98%). 1H NMR (400 MHz, CDCl3): 1.25 (t, J=7.2 Hz, 3H), 1.56 (s, 6H), 3.62 (brs, 2H), 4.23 (q, J=7.2 Hz, 2H), 6.21-6.22 (m, 2H), 6.32 (d, J=7.2 Hz, 1H), 6.99 (t, J=8.4 Hz, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionresidue was dissolved in DCM
  3. additiontreated with 2.5M solution of NaOH
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-798137bc1c264293987c8d9edcdcbdf1
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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