1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(N-(tert-butoxycarbonyl)-L-alanyl)oxy-7-methyl-3-(3-trifluoromethylphenyl)-5,6,7,8-tetrahydrocinnoline

HRID 229722

Reaktionsgleichung

Reaktionsgleichung von HRID 229722
[CH3:1][CH:2]1[CH2:11][C:10]2[N:9]=[N:8][C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)=[CH:6][C:5]=2[CH:4]([OH:22])[CH2:3]1.C(N=C=NCCCN(C)C)C.[C:34]([O:38][C:39]([NH:41][C@H:42]([C:44](O)=[O:45])[CH3:43])=[O:40])([CH3:37])([CH3:36])[CH3:35]>O1CCCC1.ClCCl>[C:34]([O:38][C:39]([NH:41][C@H:42]([C:44]([O:22][CH:4]1[CH2:3][CH:2]([CH3:1])[CH2:11][C:10]2[N:9]=[N:8][C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)=[CH:6][C:5]1=2)=[O:45])[CH3:43])=[O:40])([CH3:36])([CH3:37])[CH3:35]

Komponenten

6

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 85082Tert-butoxycarbonylalanineHCID 99725287-Methyl-3-(3-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydrocinnolin-5-ol

Produkt 1

HCID 688445095-(N-(tert-butoxycarbonyl)-L-alanyl)oxy-7-methyl-3-(3-trifluoromethylphenyl)-5,6,7,8-tetrahydrocinnoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

7-Methyl-3-(3-trifluoromethylphenyl)-5,6,7,8-tetrahydrocinnolin-5-ol (10 mg, 0.03 mmol) obtained in Example 6 was dissolved in a mixed solvent of tetrahydrofuran and dichloromethane (0.5 mL. 0.5 mL), followed by adding N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide (9 mg, 0.045 mmol), N,N-dimethylaminopyridine (catalytic amount) and N-(tert-butoxycarbonyl)-L-alanine (9 mg, 0.045 mmol) and stirring at room temperature over night. After completion of the reaction, the reaction liquid was concentrated and thus obtained residue was purified using silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain an objective compound.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. concentrationwas concentrated
  4. customthus obtained residue was purified
  5. customto obtain an objective compound

Quellen und Nachweise

ORD-Eintrag
ord-17dc1c9c39fe4caa8b43c4efcbfec233
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563893B2

Verknüpfte Notizen

Wird geladen…