Dimethyl Sulfoxide → Hydroxybosentan

HRID 397262

Reaktionsgleichung

Reaktionsgleichung von HRID 397262
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[N:20]=[C:19]([C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[N:18]=[C:17]([O:27][CH2:28][CH2:29][OH:30])[C:16]=2[O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[O:38][CH3:39])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CS(C)=[O:42]>>[OH:30][CH2:29][CH2:28][O:27][C:17]1[C:16]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[O:38][CH3:39])=[C:15]([NH:14][S:11]([C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH2:3][OH:42])=[CH:10][CH:9]=2)(=[O:12])=[O:13])[N:20]=[C:19]([C:21]2[N:22]=[CH:23][CH:24]=[CH:25][N:26]=2)[N:18]=1

Komponenten

3

Edukt 2

HCID 679Dimethyl SulfoxideHCID 104865Bosentan

Produkt 1

HCID 6426755Hydroxybosentan

Versuchsvorschrift

Streptomyces rimosus subsp. rimosus ATCC10970 maintained on a quarter strength ATCC172 agar slope was inoculated as a loopful of spores into a 300 ml Erlenmeyer flask containing 50 ml of AS-7H inoculum medium. This was allowed to incubate for 2 days at 28° C., 200 rpm on an Infors Multitron™ Shaker with 1″ throw. 2 mls of this inoculum medium was then transferred to one 300 ml Erlenmeyer flask containing 50 ml of AP-5H production medium and incubated under the same conditions for a further 24 hours. At this point 1 mg of 4-tert butyl-N-[4-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)pyrimidin-6-yl]benzenesulphonamide (CA 2071193) dissolved in 0.5 ml of dimethylsulfoxide was added to each of the flasks and the fermentation allowed to continue under the same conditions for a further 24 hours. The flask was then extracted with 200 mls of ethyl acetate and the combined ethyl acetate solubles concentrated to dryness to give a gum solid.

Aufarbeitung

  1. temperaturerimosus ATCC10970 maintained on a quarter strength ATCC172 agar slope
  2. additioncontaining 50 ml of AS-7H inoculum medium
  3. additioncontaining 50 ml of AP-5H production medium
  4. waitincubated under the same conditions for a further 24 hours
  5. additionwas added to each of the flasks
  6. waitto continue under the same conditions for a further 24 hours
  7. extractionThe flask was then extracted with 200 mls of ethyl acetate
  8. concentrationthe combined ethyl acetate solubles concentrated to dryness
  9. customto give a gum solid

Quellen und Nachweise

ORD-Eintrag
ord-6b28cc3b44ee4a6292a7b1b3ef0be398
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610518B2

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