Trifluoroacetic acid → (4-Methylamino-naphthalen-1-yloxy)-acetic Acid Ethyl Ester

HRID 1726962Notes

Reaction equation

HRID 1726962 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([N:17](C(OC(C)(C)C)=O)[CH3:18])=[CH:9][CH:8]=1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([NH:17][CH3:18])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69035131[4-(Tert-butoxycarbonyl-methyl-amino)-naphthalen-1-yloxy]-acetic acid ethyl ester

Product 1

HCID 69037388(4-Methylamino-naphthalen-1-yloxy)-acetic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3.90 g (10.9 mmol) of the above prepared [4-(tert-butoxycarbonyl-methyl-amino)-naphthalen-1-yloxy]-acetic acid ethyl ester, dissolved in 110 ml of CH2Cl2, was added via dropping funnel within 15 Min. 27.9 ml of TFA. After additional 30 Min. at RT, the bulk of the solvents was removed i. V. and the residue distributed between NaHCO3 and AcOEt. Washing with cold water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=8/2), gave 2.25 g of the title compound as off-white crystals.

Workup

  1. additionwas added
  2. customat RT, the bulk of the solvents was removed i
  3. washWashing with cold water and brine
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-378f09cb1be14cb286bf3e4fb1f5004f
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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