tert-Butyl-1-(benzoylcarbamothioyl)-6a-phenyl-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate → tert-Butyl(3S,4R)-3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylate

HRID 1619015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619015
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[C:10]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([N:11]([C:16](=[S:26])[NH:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:12][CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Zn].C(O)(=O)C>[C:18]([NH:17][C:16]([NH:11][C@:10]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@H:14]([CH2:13][OH:12])[CH2:15][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)=[S:26])(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

4

Edukt 1

HCID 86697923tert-Butyl-1-(benzoylcarbamothioyl)-6a-phenyl-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate

Produkt 1

HCID 86697927tert-Butyl(3S,4R)-3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of tert-butyl-1-(benzoylcarbamothioyl)-6a-phenyl-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate (2.3 g, 5.1 mmol), acetic acid (20 mL), and powdered zinc (3.3 g, 50 mmol) is vigorously stirred at 40° C. for 1 hour, followed by an additional hour at 45-50° C. The reaction is concentrated under reduced pressure. To the residue is added diatomaceous earth and water, followed by a saturated solution of sodium bicarbonate. The mixture is filtered and washed with ethyl acetate. The filtrate is extracted with ethyl acetate. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1) to give the title compound (1.6 g, 70%). ES/MS (m/e): 456 (M+H).

Aufarbeitung

  1. waitfollowed by an additional hour at 45-50° C
  2. concentrationThe reaction is concentrated under reduced pressure
  3. additionTo the residue is added diatomaceous earth and water
  4. filtrationThe mixture is filtered
  5. washwashed with ethyl acetate
  6. extractionThe filtrate is extracted with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give a residue
  11. customThe residue is purified by silica gel flash chromatography
  12. washeluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1)

Quellen und Nachweise

ORD-Eintrag
ord-99d9d97482b54ad181910cec7b297f32
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772282B2

Notizen zur Reaktion

Wird geladen…