Lithium Hydroxide → HCID 67691019, Verbindung

HRID 484444

Reaktionsgleichung

Reaktionsgleichung von HRID 484444
C[O:2][C:3]([C@H:5]1[CH2:14][C@H:13]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:19]=2)=[O:17])[C:12]2[C:7](=[CH:8][C:9]([Cl:34])=[CH:10][C:11]=2[Cl:33])[NH:6]1)=[O:4].[OH-].[Li+]>O1CCCC1.O>[C:3]([C@H:5]1[CH2:14][C@H:13]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH:19]=2)=[O:17])[C:12]2[C:7](=[CH:8][C:9]([Cl:34])=[CH:10][C:11]=2[Cl:33])[NH:6]1)([OH:4])=[O:2]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 67690889Trans-2-methoxycarbonyl-5,7-dichloro-4-(3-tertbutyloxycarbonylaminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline

Produkt 1

HCID 67691019HCID 67691019, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of trans-2-methoxycarbonyl-5,7-dichloro-4-(3-tert-butyloxycarbonylaminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline (step b) (430 mg, 0.846 mmol) in a mixture of tetrahydrofuran (20 ml) and water (10 ml) was added aqueous lithium hydroxide (1.95 ml of a 0.5M solution, 0.973 mmol), and the resulting mixture was stirred at room temperature for 3 h. The organic solvent was removed in vacuo and the aqueous residue was diluted to 50 ml before acidifying to pH 1 with 1N HCl. The white precipitate was extracted into ethyl acetate (150 ml), washed with brine and dried (Na2SO4). The solution was evaporated to give a residue which was washed with diethyl ether and collected by filtration to give the title compound as a colourless crystalline solid, m.p. 192°-193° C. δ (DMSO, 360 MHz) 1.39 (9H, s, C(CH3)3, 1.73 (1H, ddd, 13.2, 13.0 and 3.8 Hz, CHACHBHCCHD), 2.26 (1H, dm, J=13.2 Hz, CHACHBHCCHD), 3.96 (1H, dd, J=13.0 and 3.0 Hz, CHACHBHCCHD), 4.14 (2H, d,J=5.6 Hz, ArCH2NH), 5.26 (1H, m, CHACHBHCCHD), 6.65 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.82 (1H, br s, ArNHCO), 6.91 (1H, d, J=2.0 Hz, 6-H or 8-H). 7.36-7.37 and 7.72-7.76 (5H, m, Ar-H and CH2NHCO), 8.66 (1H, d, J=7 Hz, NHCOAr); m/e (FAB+), 494 (M+1), 93 (100%); Found C, 55.92; H, 5.22; N, 8.35; C23H25Cl2N3O5 requires C, 55.88; H, 5.10; N, 8.50%.

Aufarbeitung

  1. customThe organic solvent was removed in vacuo
  2. additionthe aqueous residue was diluted to 50 ml
  3. extractionThe white precipitate was extracted into ethyl acetate (150 ml)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solution was evaporated
  7. customto give a residue which
  8. washwas washed with diethyl ether
  9. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-4fb36bb4a3ec4d43a72e427dae837be8
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05231102

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