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Trifluoroacetic acid → (S,S)-3-[2-(3-Acetylamino-2-oxo-2H-pyridin-1-yl)-butyrylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid

HRID 2422691
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2422691
C([O:5][C:6](=[O:40])[CH2:7][C@H:8]([NH:23][C:24](=[O:39])[C@@H:25]([N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:35](=[O:37])[CH3:36])[C:29]1=[O:38])[CH2:26][CH3:27])[C:9](=[O:22])[CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:35]([NH:34][C:30]1[C:29](=[O:38])[N:28]([C@@H:25]([CH2:26][CH3:27])[C:24]([NH:23][C@H:8]([C:9](=[O:22])[CH2:10][O:11][C:12]2[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=2[F:21])[CH2:7][C:6]([OH:40])=[O:5])=[O:39])[CH:33]=[CH:32][CH:31]=1)(=[O:37])[CH3:36]
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 11592245(S,S)-3-[2-(3-Acetylamino-2-oxo-2H-pyridin-1-yl)-butyrylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

Produkt 1

HCID 11477827(S,S)-3-[2-(3-Acetylamino-2-oxo-2H-pyridin-1-yl)-butyrylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acidAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A solution of (S,S)-3-[2-(3-Acetylamino-2-oxo-2H-pyridin-1-yl)-butyrylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester (187 mg, 0.327 mmol) in dichloromethane (5 mL) was cooled to 0° C. Trifluoroacetic acid (5 ml) was added and the resulting mixture allowed to warm to room temperature and stir for 2 hours. The mixture was then concentrated under reduced pressure and the residue redissolved in dichloromethane. This process was repeated several times in order to remove excess trifluoroacetic acid. The resulting solid was slurried in diethyl ether, filtered and washed with more diethyl ether. The solid was then dried to constant weight under vacuum. This gave the title product as a white solid (138 mg, 82%); 1H NMR (400 MHz, d6-DMSO) δ 0.78 (3H, t), 1.87-2.13 (5H, m), 2.56-2.78 (2H, m), 4.62 (1H, m), 5.18-5.29 (2H, m), 5.40 (1H, m), 6.28 (1H, t), 7.37 (1H, d), 7.53-7.66 (1H, m), 8.17-8.21 (1H, m), 8.92 (1H, d), 9.21 (1H, s), 12.51 (1H, br s); 19F NMR (376 MHz, d6-DMSO, proton-decoupled) δ−156.9, −141.1; M+H 516.2, M−H 514.2.

Aufarbeitung

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. dissolutionthe residue redissolved in dichloromethane
  3. customto remove excess trifluoroacetic acid
  4. filtrationfiltered
  5. washwashed with more diethyl ether
  6. customThe solid was then dried to constant weight under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-99652b8c7ec945ac896d7240f883a4b5
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07960415B2

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