Acetic Anhydride → N-[4-[5-(Cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-acetoxy-3-methyl-but-1-yn-1-yl)-benzenesulfonamide

HRID 6384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 6384
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH:8]1([O:13][C:14]([NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[CH:21]=[C:20]3[CH2:27][C:28]2[CH:51]=[CH:50][C:31]([C:32]([NH:34][S:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[C:44]#[C:45][C:46]([OH:49])([CH3:48])[CH3:47])(=[O:37])=[O:36])=[O:33])=[CH:30][C:29]=2[O:52][CH3:53])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(OCC)(=O)C>[CH:8]1([O:13][C:14]([NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[CH:21]=[C:20]3[CH2:27][C:28]2[CH:51]=[CH:50][C:31]([C:32]([NH:34][S:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[C:44]#[C:45][C:46]([O:49][C:1](=[O:3])[CH3:2])([CH3:48])[CH3:47])(=[O:36])=[O:37])=[O:33])=[CH:30][C:29]=2[O:52][CH3:53])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1

Komponenten

6

Edukt 2

HCID 7918Acetic AnhydrideHCID 19793571N-[4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-hydroxy-3-methyl-but-1-yn-1-yl)-benzenesulfonamide

Produkt 1

HCID 67884075N-[4-[5-(Cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-acetoxy-3-methyl-but-1-yn-1-yl)-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.44 g of acetic anhydride and 0.1 g of 4-dimethylaminopyridine are added to a solution of 1.0 g of N-[4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-hydroxy-3-methyl-but-1-yn-1-yl)-benzenesulfonamide in 6 ml of pyridine. The reaction solution is stirred for 20 hours at room temperature under argon. The reaction mixture is subsequently diluted with 100 ml of ethyl acetate. The ethyl acetate phase is washed twice with 80 ml of 1N hydrochloric acid each time, with 50 ml of water and with 50 ml of saturated sodium chloride solution. The ethyl acetate phase is dried over magnesium sulfate and concentrated by evaporation at 20 torr and 40°. The residue is chromatographed on 50 g of silica gel (Merck, ST 60, 40-63 μm) with hexane/ethyl acetate=1/1 to yield the title compound in the form of a white amorphous solid. 1H-NMR (400 MHz, DMSO-d6): 8.87 (b, 1H); 8.06 (d, d, 1H); 7.61 (m, 3H); 7.55 (d, 1H); 7.50 (d, 1H); 7.41 (d, d, 1H); 7.22 (d, 1H); 7.14 (d, d, 1H); 7.13 (d, 1H); 6.94 (s, 1H); 5.06 (m, 1H); 3.95 (s, 2H); 3.90 (s, 3H); 3.66 (s, 3H); 1.91 (s, 3H); 1.89-1.52 (m, 8H); 1.61 (s, 6H).

Aufarbeitung

  1. washThe ethyl acetate phase is washed twice with 80 ml of 1N hydrochloric acid each time
  2. dry with materialThe ethyl acetate phase is dried over magnesium sulfate
  3. concentrationconcentrated by evaporation at 20 torr and 40°
  4. customThe residue is chromatographed on 50 g of silica gel (Merck, ST 60, 40-63 μm) with hexane/ethyl acetate=1/1

Quellen und Nachweise

ORD-Eintrag
ord-a0f180715a4a474e864218093f7ef149
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248693

Notizen zur Reaktion

Wird geladen…