3-Chlorobenzenesulphonyl chloride → (S,S)-2-(3-Chloro-benzenesulfonylamino)-3-cyclohexyl-N-[1-methyl-2-(4-trifluoromethoxy-phenylamino)-ethyl]-propionamide

HRID 132149

Reaktionsgleichung

Reaktionsgleichung von HRID 132149
[NH2:1][C@@H:2]([CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:3]([NH:5][C@@H:6]([CH3:20])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)=[O:4].[Cl:28][C:29]1[CH:30]=[C:31]([S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.CO>[Cl:28][C:29]1[CH:30]=[C:31]([S:35]([NH:1][C@@H:2]([CH2:21][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[C:3]([NH:5][C@@H:6]([CH3:20])[CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:17])([F:18])[F:19])=[CH:11][CH:10]=2)=[O:4])(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1

Komponenten

6

Edukt 2

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 59818058HCID 59818058, Verbindung

Produkt 1

HCID 59733159(S,S)-2-(3-Chloro-benzenesulfonylamino)-3-cyclohexyl-N-[1-methyl-2-(4-trifluoromethoxy-phenylamino)-ethyl]-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

The product from step D (15.4 mg, 39.7 μmol) was added to a flask with DMAP (14.5 mg, 0.119 mmol) and dry DMF (0.5 mL). 3-Chloro-benzenesulfonyl chloride (8.37 mg, 39.7 μmol) was added as a solution in 0.5 mL of dry DMF dropwise over 3 minutes. The resulting solution was stirred for 12 hours and the volatiles were stripped off. The solids were taken up in methanol and purified by prep HPLC. Yield 15 mg, 67%. 1H NMR (CDCl3) δ(ppm): 7.9 (s, 1H), 7.75 (d, J=7.9 Hz, 1H), 7.6 (d, J=8 Hz, 1H), 7.5 (t, J=7.9 Hz, 1H), 7.05 (d, J=8.3 Hz, 2H), 6.6 (d, J=8.9 Hz, 2H), 6.15 (s, 1H), 5.1 (s, 1H), 4.1 (m, 1H), 3.65 (m, 1H), 3.25 (dd J=4.7, 12.9 Hz, 1H), 3.1 (dd J=7.5, 12.7 Hz, 1H), 1.6 (m, 7H), 1.4 (m, 1H), 1.3 (m, 1H), 1.2 (d, J=8.4 Hz, 3H), 1.07 (m, 3H), 0.65 (m, 1H). C25H31CWF3N3O4S: LC/MS=562.2 (M+1).

Aufarbeitung

  1. custompurified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7a7c5a4787984f5b86d411988ba84448
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384970B2

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