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N-(4'-chloro-2'-fluoro-5'-isopropyloxyphenyl)-3-(trifluoromethyl)glutaramic acid → N-(4'-chloro-2'-fluoro-5'-isopropyloxyphenyl)-5-hydroxy-3-(trifluoromethyl)pentanamide

HRID 2255173
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2255173
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([NH:12][C:13](=[O:24])[CH2:14][CH:15]([C:20]([F:23])([F:22])[F:21])[CH2:16][C:17](O)=[O:18])=[C:4]([F:25])[CH:3]=1.[Na].C(C1C=CC=CC=1)(=O)C1C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([NH:12][C:13](=[O:24])[CH2:14][CH:15]([C:20]([F:22])([F:21])[F:23])[CH2:16][CH2:17][OH:18])=[C:4]([F:25])[CH:3]=1
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Komponenten

4

Edukt 2

HCID 19047101N-(4'-chloro-2'-fluoro-5'-isopropyloxyphenyl)-3-(trifluoromethyl)glutaramic acidHCID 66591377Sodium benzophenone

Produkt 1

HCID 19047170N-(4'-chloro-2'-fluoro-5'-isopropyloxyphenyl)-5-hydroxy-3-(trifluoromethyl)pentanamideAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-(4'-chloro-2'-fluoro-5'-isopropyloxyphenyl)-3-(trifluoromethyl)glutaramic acid (4.32 g, 11.4 mmol) in 20 ml of tetrahydrofuran, (freshly distilled from sodium/benzophenone) was slowly added 10M borane-methyl sulfide complex (1.18 ml) via syringe. The temperature was maintained at 10°-20° C. with an ice bath while vigorous bubbling was evident. The mixture was allowed to warm slowly to room temperature and stirred 150 hrs while kept under nitrogen, heated to 55° C. for 6 hours, then cooled to room temperature and allowed to stand for 16 hours. The flask was cooled in an ice/water bath, then 7 ml of methanol (MeOH) were added slowly via addition funnel. The reaction mixture became too thick to continue stirring. It was allowed to warm slowly to room temperature, when the stir bar was again able to stir the mixture. The MeOH and THF were removed in vacuo (20-50 Torr) and the residue was flash chromatographed (2"×7" column, 3:1 hexanes/ethyl acetate, 75 ml fractions). Fractions 18-45 were combined and the solvent was removed in vacuo. The residue was dried in the vacuum oven at 50° C. to yield 1.66 g (39% yield) of the pentanamide as a nearly colorless oil.

Aufarbeitung

  1. temperatureThe temperature was maintained at 10°-20° C. with an ice bath
  2. customwhile vigorous bubbling
  3. temperatureheated to 55° C. for 6 hours
  4. temperaturecooled to room temperature
  5. waitto stand for 16 hours
  6. temperatureThe flask was cooled in an ice/water bath
  7. addition7 ml of methanol (MeOH) were added slowly via addition funnel
  8. stirringto continue stirring
  9. temperatureto warm slowly to room temperature
  10. stirringto stir the mixture
  11. customThe MeOH and THF were removed in vacuo (20-50 Torr)
  12. customchromatographed (2"×7" column, 3:1 hexanes/ethyl acetate, 75 ml fractions)
  13. customthe solvent was removed in vacuo
  14. customThe residue was dried in the vacuum oven at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-fefbb29212fb43ae9b5d77397d4588cf
Quelldatensatz
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05238908

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