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Ammonia → (S)-4-Amino-N-(1-cyano-2-(3'-cyanobiphenyl-4-yl)ethyl)tetrahydro-2H-pyran-4-carboxamide

HRID 216924
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 216924
[C:1]([C@@H:3]([NH:19][C:20]([C:22]1([NH:28]C(=O)OC(C)(C)C)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=2)=[CH:7][CH:6]=1)#[N:2].O.N>C(O)=O>[NH2:28][C:22]1([C:20]([NH:19][C@H:3]([C:1]#[N:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=3)=[CH:9][CH:10]=2)=[O:21])[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 962WaterHCID 59568588(S)-tert-butyl 4-(1-cyano-2-(3'-cyanobiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Produkt 1

HCID 49783746(S)-4-Amino-N-(1-cyano-2-(3'-cyanobiphenyl-4-yl)ethyl)tetrahydro-2H-pyran-4-carboxamideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284
Formic Acid
Lösungsmittel

Reaktionsbedingungen

Temperatur
36 °C

Versuchsvorschrift

(S)-tert-butyl 4-(1-cyano-2-(3′-cyanobiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 8, step (ii), 282 mg) in formic acid (1.5 mL) was stirred at room temperature for 5 h, warmed at 36° C. for 30 mins then stirred at room temperature overnight. Water was added and the cooled solution was made basic with 0.880 ammonia and then extracted (×3) with dichloromethane. The combined organic extracts were dried over magnesium sulphate, filtered and the solvent was evaporated to yield an oil which was purified by chromatography on silica using 80% ethyl acetate in isohexane as eluent and then crystallised from isopropanol to yield a solid. The solid was washed with diethyl ether and dried to afford the titled compound (89 mg).

Aufarbeitung

  1. extractionextracted (×3) with dichloromethane
  2. dry with materialThe combined organic extracts were dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customto yield an oil which
  6. customwas purified by chromatography on silica using 80% ethyl acetate in isohexane as eluent
  7. customcrystallised from isopropanol
  8. customto yield a solid
  9. washThe solid was washed with diethyl ether
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9641d5bc9e7345cbb8b7009d1582c899
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08193239B2

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