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Hydrochloric Acid → 1,1-dimethylethyl (3S)-3-{[4-(4-bromo-2-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-1-pyrrolidinecarboxylate

HRID 2405431
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2405431
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][NH:12][C:13](=O)[CH2:14][C@@H:15]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]2)=[O:10])=[C:4]([F:28])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.Cl>C(OCC)(=O)C.C(O)CC.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[O:10])[NH:11][N:12]=[C:13]2[CH2:14][C@@H:15]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]2)=[C:4]([F:28])[CH:3]=1
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Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 866748271,1-dimethylethyl (3S)-3-[2-(2-{[(4-bromo-2-fluorophenyl)amino]carbonyl}hydrazino)-2-oxoethyl]-1-pyrrolidinecarboxylate

Produkt 1

HCID 673758561,1-dimethylethyl (3S)-3-{[4-(4-bromo-2-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-1-pyrrolidinecarboxylate
Ausbeute 41,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 10311-PropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Into a 250 mL round bottom flask was placed 1,1-dimethylethyl (3S)-3-[2-(2-{[(4-bromo-2-fluorophenyl)amino]carbonyl}hydrazino)-2-oxoethyl]-1-pyrrolidinecarboxylate (4.35 mmol). Added to the flask was K2CO3 (21.71 mmol), water (100 mL), and 1-propanol (10.00 mL). The solution was stirred at reflux (140° C.) for 16 h and then cooled to room temperature and filtered to remove an undetermined solid. The filtrate was concentrated in vacuo. Added to the white solid was 1N aq NaOH (10 mL) followed by the addition of Boc2O (4.35 mmol). The solution was stirred at room temperature overnight. The solution was diluted with 100 mL ethyl acetate and brought to a pH=7 with the addition of 1N aq HCl. The organic layer was separated and the aqueous layer was washed twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel purification (100% dichloromethane, 0-100% ethyl acetate, and 0-10% methanol:ethyl acetate) provided the title product (790 mg, 39%). MS(ES)+ m/e 442.0, 443.0 [M+H]+.

Aufarbeitung

  1. customInto a 250 mL round bottom flask was placed
  2. additionAdded to the flask
  3. temperaturecooled to room temperature
  4. filtrationfiltered
  5. customto remove an undetermined solid
  6. concentrationThe filtrate was concentrated in vacuo
  7. additionAdded to the white solid
  8. stirringThe solution was stirred at room temperature overnight
  9. customThe organic layer was separated
  10. washthe aqueous layer was washed twice with ethyl acetate
  11. dry with materialThe combined organic layers were dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customSilica gel purification (100% dichloromethane, 0-100% ethyl acetate, and 0-10% methanol:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6a3374be734f4c979e5834c7f652d4e0
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08802864B2

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