Trifluoroacetic acid → 5-[4-(Benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amide

HRID 545620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545620
C(OC([CH:8]1[CH:12]2[CH2:13][N:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[S:25][C:26]5[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=5[N:28]=4)=[CH:19][CH:18]=3)[CH2:15][CH:11]2[CH2:10][N:9]1[S:33]([NH2:36])(=[O:35])=[O:34])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.CO.CS(C)=O>[S:25]1[C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=[C:24]1[O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:14]2[CH2:15][CH:11]3[CH2:10][N:9]([S:33]([NH2:36])(=[O:34])=[O:35])[CH2:8][CH:12]3[CH2:13]2)=[CH:22][CH:21]=1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86629966Tert-butoxy carbonyl-5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amide

Produkt 1

HCID 426005665-[4-(Benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 22036561Dimethyl sulfoxide methanolLösungsmittel

Versuchsvorschrift

To a stirred solution tert-butoxy carbonyl-5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amide (108 mg, 0.20 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (1 mL). The homogeneous reaction mixture was allowed to stir overnight at rt. The crude reaction mixture was blown down to dryness and dissolved in CH3OH/DMSO (2:1) and purified via reverse phase preparative HPLC to afford the title compound as fluffy white powder (60 mg, 70%). MS (ESI): mass calcd. for C20H22N4O3S2, 430.6; m/z found, 431.1 [M+H]+; 1H NMR (500 MHz, CD3OD): 7.79 (d, J=8.0 Hz, 1H), 7.67 (d, J=8.1 Hz, 1H), 7.52-7.46 (m, 2H), 7.46-7.39 (m, 1H), 7.37-7.27 (m, 3H), 3.68 (s, 2H), 3.24 (dd, J=9.5, 7.0 Hz, 2H), 3.06 (dd, J=9.4, 2.6 Hz, 2H), 2.93-2.87 (m, 2H), 2.87-2.78 (m, 2H), 2.40 (dd, J=8.5, 3.6 Hz, 2H).

Aufarbeitung

  1. customThe crude reaction mixture
  2. custompurified via reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-90f5b99246c24c5097d7e4216b33fbd1
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935725B2

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