Reaktion #1929041

ord-90a0cbf4979747328309e27b78a286ee

Reaktionsgleichung

CCC1(OC(=O)COc2c(C)cc(-[s+]3c4ccccc4c4ccccc43)cc2C)CCCC1.[Br-]
5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide
C[C@H](CCC(=O)OCCC(F)(F)C(F)(F)S(=O)(=O)[O-])[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(=O)CC[C@]4(C)[C@H]3CC(=O)[C@]12C.[Na+]
sodium 4-((4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyloxy)-1,1,2,2-tetrafluorobutane-1-sulfonate
O
water
→
CCC1(OC(=O)COc2c(C)cc(-[s+]3c4ccccc4c4ccccc43)cc2C)CCCC1.C[C@H](CCC(=O)OCCC(F)(F)C(F)(F)S(=O)(=O)[O-])[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(=O)CC[C@]4(C)[C@H]3CC(=O)[C@]12C
title compound
Ausbeute 80.2%
CCC1(OC(=O)COc2c(C)cc(-[s+]3c4ccccc4c4ccccc43)cc2C)CCCC1.C[C@H](CCC(=O)OCCC(F)(F)C(F)(F)S(=O)(=O)[O-])[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(=O)CC[C@]4(C)[C@H]3CC(=O)[C@]12C
5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium 4-((4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyloxy)-1,1,2,2-tetrafluorobutane-1-sulfonate
Ausbeute 80.2%

Edukte

CCC1(OC(=O)COc2c(C)cc(-[s+]3c4ccccc4c4ccccc43)cc2C)CCCC1.[Br-]
5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide
C[C@H](CCC(=O)OCCC(F)(F)C(F)(F)S(=O)(=O)[O-])[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(=O)CC[C@]4(C)[C@H]3CC(=O)[C@]12C.[Na+]
sodium 4-((4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyloxy)-1,1,2,2-tetrafluorobutane-1-sulfonate
O
water

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe dichloromethane layer was separated
  2. 2
    Waschenthe aqueous phase washed with dichloromethane (3×250 mL)
  3. 3
    WaschenThe combined organic layers were washed with water (4×250 mL)
  4. 4
    Einengenconcentrated in vacuo and residual water
  5. 5
    Sonstigeremoved via azeotrope with acetonitrile (2×250 mL)

Vorschrift

5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide (4.20 g, 7.79 mmol) and sodium 4-((4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyloxy)-1,1,2,2-tetrafluorobutane-1-sulfonate (4.78 g, 7.56 mmol) were dissolved in dichloromethane (225 mL) and water (225 mL) and stirred at room temperature overnight. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×250 mL). The combined organic layers were washed with water (4×250 mL), concentrated in vacuo and residual water removed via azeotrope with acetonitrile (2×250 mL) to afford the title compound (6.48 g, 80%) as a white solid. 1H NMR (500 MHz, (CD3)2CO) δ: 8.53 (d, J=8 Hz, 2H), 8.37 (d, J=8 Hz, 2H), 8.04 (t, J=7.5 Hz, 2H), 7.85 (t, J=7.5 Hz, 2H), 7.52 (s, 2H), 4.57 (s, 2H), 4.32 (t, J=7 Hz, 2H), 3.06-3.17 (m, 3H), 2.95 (t, J=12.5 Hz, 1H), 2.66-2.83 (m, 3H), 2.2-2.54 (m, 8H), 1.57-2.14 (m, 13H), 1.48 (s, 3H), 1.25-1.41 (m, 7H), 1.90-1.12 (m, 6H), 0.82-0.89 (m, 9H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08945814B2uspto-grants-2015_02