Trifluoroacetic acid → 1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-(2-{N-[(R)-alpha-(carboxy)benzyl]carbamoyl}ethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepine

HRID 458905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 458905
[O:1]=[S:2]1(=[O:46])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][CH2:16][C:17](=[O:33])[NH:18][C@@H:19]([C:26]([O:28]C(C)(C)C)=[O:27])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:11]([Br:13])=[CH:12][C:7]=2[N:6]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:5][C:4]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:40][CH3:41])[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:46]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][CH2:16][C:17](=[O:33])[NH:18][C@@H:19]([C:26]([OH:28])=[O:27])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:11]([Br:13])=[CH:12][C:7]=2[N:6]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:5][C:4]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:40][CH3:41])[CH2:3]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 693605551,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-(2-{N-[(R)-alpha-(t-butoxycarbonyl)benzyl]carbamoyl}ethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepine

Produkt 1

HCID 693615141,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-(2-{N-[(R)-alpha-(carboxy)benzyl]carbamoyl}ethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepineAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1,1-dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-(2-{N-[(R)-α-(t-butoxycarbonyl)benzyl]carbamoyl}ethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 90; 77 mg, 0.108 mmol) in DCM (3 ml) was added at 0° C. TFA (0.75 ml). The reaction mixture was stirred at room temperature for 2 h and 45 min. The solvent was evaporated under reduced pressure and the crude product was purified by preparative HPLC using MeCN and ammonium acetate buffer (40:60 to 50:50) as eluent to give the title compound 60 mg (82%). NMR (500 MHz, CD3OD) 0.75–0.85 (m, 6H), 1.0–1.25 (m, 4H), 1.40–1.64 (m, 4H), 2.75–2.90 (m, 2H), 3.26 (s, 2H), 3.50–3.90 (m, 2H), 4.30–4.41 (m, 2H), 5.43 (s, 1H), 6.99 (t, 1H), 7.05–7.13 (m, 3H), 7.23–7.34 (m, 5H), 7.45 (d, 2H), 7.52 (s, 1H); m/z 658.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b62bdec40f5540a08a6dd93b4a2f71cc
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192945B2

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