Trifluoroacetic acid → [4-(2-{[2-(Methoxycarbonyl)phenyl]thio}ethyl)phenoxy]acetic acid

HRID 898901

Reaktionsgleichung

Reaktionsgleichung von HRID 898901
C([O:5][C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:23][O:22][C:20]([C:19]1[CH:24]=[CH:25][CH:26]=[CH:27][C:18]=1[S:17][CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]([OH:28])=[O:5])=[CH:14][CH:13]=1)=[O:21]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 69259277Methyl 2-({2-[4-(2-tert-butoxy-2-oxoethoxy)phenyl]ethyl}thio)benzoate

Produkt 1

HCID 57640312[4-(2-{[2-(Methoxycarbonyl)phenyl]thio}ethyl)phenoxy]acetic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 2-({2-[4-(2-tert-butoxy-2-oxoethoxy)phenyl]ethyl}thio)benzoate (4.630 g, 11.502 mmol) was taken up into DCM (50 ml) and treated with trifluoroacetic acid (44.40 g, 389.405 mmol) at RT for 4 h. The mixture was evaporated and azeotroped with toluene. The crude was purified by preparative HPLC (the initial mobile phase was isocratic acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min). The product containing fractions were pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4). The solvent was removed by evaporation to give 3.825 g of [4-(2-{[2-(methoxycarbonyl)phenyl]-thio}ethyl)-phenoxy]acetic acid (yield for two steps 63.9% overall).

Aufarbeitung

  1. customThe mixture was evaporated
  2. customazeotroped with toluene
  3. customThe crude was purified by preparative HPLC (the initial mobile phase
  4. concentrationthe acetonitrile concentration
  5. temperaturewas increased to 100%
  6. additiona mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)
  7. additionThe product containing fractions
  8. customthe acetonitrile was removed by evaporation
  9. additionEtOAc (10 ml) was added
  10. washthe organic phase was washed with two portions of brine
  11. dry with materialdried (MgSO4)
  12. customThe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-0a004aa303394581beaeb3aa2bcb9b1d
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351858B2

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