HCID 57654653, Verbindung → HCID 57654650, Verbindung

HRID 1175129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1175129
[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([Cl:19])[CH:17]=3)[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2].O(C(C)(C)C)[Li].[C:26]([O:30][C:31]([N:33]1[CH2:36][C:35]([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])([CH2:37]OS(C)(=O)=O)[CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:37][C:35]2([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:34][N:33]([C:31]([O:30][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:32])[CH2:36]2)[N:8]=[C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([Cl:19])[CH:17]=3)[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 57654653HCID 57654653, VerbindungHCID 59558516HCID 59558516, VerbindungHCID 178506942HCID 178506942, Verbindung

Produkt 1

HCID 57654650HCID 57654650, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

8-Chloro-4,5-dihydro-2H-1,2,7-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester (320 mg; 1.15 mmol) in DMF (4 ml) is treated at 5° C. with LiOtBu (1N in THF; 1.16 ml; 1.16 m mol) for 5 minutes. 3-tert-butoxycarbonylamino-3-methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester (0.32 mg; 1.15 mmol) is added and the mixture heated to 90° C. for 30 minutes. The reaction mixture is poured on brine and extracted with TBME three times. The combined organic phases are dried over Na2SO4, evaporated to dryness and yield the title compound as colorless crystals. 1H-NMR (400 MHz; DMSO-d6: 8.38 (s, 1H); 7.65 (s, 1H); 7.42 (bs, 1H); 5.00 (bs, 2H); 4.34 (q, 2H); 4.03 (bd, 2H); 3.79 (m, 2H); 3.00 (m, 2H); 2.95 (m, 2H); 1.40 (s, 18H); 1.36 (t, 3H). MS (m/z) ES+: 562 (MH+).

Aufarbeitung

  1. additionThe reaction mixture is poured on brine
  2. extractionextracted with TBME three times
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a3114a6d24574eb4bd05c95c22fe752e
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838674B2

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