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

HRID 1726962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1726962
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-378f09cb1be14cb286bf3e4fb1f5004f
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495001B2

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