Trifluoroacetic acid → 2-(3-Methoxy-propyl)-4-methylamino-phenoxy-acetic acid ethyl ester

HRID 1393098Notes

Reaction equation

HRID 1393098 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13](C(OC(C)(C)C)=O)[CH3:14])=[CH:9][C:8]=1[CH2:22][CH2:23][CH2:24][O:25][CH3:26])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH3:14])=[CH:9][C:8]=1[CH2:22][CH2:23][CH2:24][O:25][CH3:26])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670721854-(tert-Butoxycarbonyl-methyl-amino)-2-(3-methoxy-propyl)-phenoxy-acetic acid ethyl ester

Product 1

HCID 670721342-(3-Methoxy-propyl)-4-methylamino-phenoxy-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.55 g (4.06 mmol) of the above prepared [4-(tert-butoxycarbonyl-methyl-amino)-2-(3-methoxy-propyl)-phenoxy]-acetic acid ethyl ester was dissolved in 41 ml of CH2Cl2 and treated dropwise with 10 ml of TFA. After additional 30 min at RT, the bulk of the solvents was removed i. V. and the residue distributed between cold NaHCO3-solution and EtOAc. Washing with cold water and brine, drying over magnesium sulfate, and evaporation of the solvents left 1.15 g of the title compound as brownish oil which was used as such for the next step.

Workup

  1. customthe bulk of the solvents was removed i
  2. washWashing with cold water and brine
  3. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  4. waitleft 1.15 g of the title compound as brownish oil which

Sources & evidence

ORD record
ord-b7c2e8202c5d4d6dad7bf20a008417f3
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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