Reaktion #1111293

ord-9525c395e0744228b4e33d04d4591819

Reaktionsgleichung

CCCCCC(O)c1ccc(C2=C(O)C(=O)C[C@@H]2CCCc2ccc(C(=O)OC)s2)cc1
31
CCCCCC(O)c1ccc(C2=C(O)C(=O)C[C@@H]2CCCc2ccc(C(=O)OC)s2)cc1
5-(3-{(S)-3-Hydroxy-2-[4-(1-hydroxy-hexyl)-phenyl]-4-oxo-cyclopent-2-enyl}-propyl)-thiophene-2-carboxylic acid methyl ester
CS(C)=O
DMSO
O=P([O-])([O-])[O-]
phosphate
→
CCCCCC(O)c1ccc(C2=C(O)C(=O)C[C@@H]2CCCc2ccc(C(=O)O)s2)cc1
title compound
Ausbeute 21.0%
CCCCCC(O)c1ccc(C2=C(O)C(=O)C[C@@H]2CCCc2ccc(C(=O)O)s2)cc1
5-(3-{(S)-3-Hydroxy-2-[4-(1-hydroxy-hexyl)-phenyl]-4-oxo-cyclopent-2-enyl}-propyl)-thiophene-2-carboxylic acid
Ausbeute 21.0%

Edukte

CCCCCC(O)c1ccc(C2=C(O)C(=O)C[C@@H]2CCCc2ccc(C(=O)OC)s2)cc1
31
CCCCCC(O)c1ccc(C2=C(O)C(=O)C[C@@H]2CCCc2ccc(C(=O)OC)s2)cc1
5-(3-{(S)-3-Hydroxy-2-[4-(1-hydroxy-hexyl)-phenyl]-4-oxo-cyclopent-2-enyl}-propyl)-thiophene-2-carboxylic acid methyl ester
CS(C)=O
DMSO
O=P([O-])([O-])[O-]
phosphate

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with H2O and brine
  2. 2
    TrocknenThe resulting organic solution was dried (Na2SO4)
  3. 3
    Filtrationfiltered
  4. 4
    Sonstigeevaporated
  5. 5
    SonstigePurification by flash chromatography on silica gel (0%→30% methanol/dichloromethane)

Vorschrift

A mixture of 31 (5 mg, 0.011 mmol), rabbit liver esterase (3 mg, Aldrich), DMSO (50 μL) and pH 7.2 phosphate buffer (0.5 mL) was stirred at room temperature overnight. The reaction was diluted with CH2Cl2 and washed with H2O and brine. The resulting organic solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (0%→30% methanol/dichloromethane) gave the title compound (1 mg, 21%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08722726B2uspto-grants-2014_05