Sodium Bicarbonate → {1-Benzyl-2-hydroxy-3-[isobutyl-(2-oxo-2,3-dihydro-1H-indole-5-sulfonyl)-amino]-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

HRID 1158257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158257
[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:28])[NH:11][CH:12]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:13]([OH:20])[CH2:14][NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:2]1.C(=O)(O)[O-].[Na+].[O:34]=[C:35]1[CH2:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([S:44](Cl)(=[O:46])=[O:45])[CH:41]=2)[NH:36]1>C(Cl)Cl.C(OCC)(=O)C>[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:28])[NH:11][CH:12]([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:13]([OH:20])[CH2:14][N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[S:44]([C:40]2[CH:41]=[C:42]3[C:37](=[CH:38][CH:39]=2)[NH:36][C:35](=[O:34])[CH2:43]3)(=[O:45])=[O:46])[CH2:2]1

Komponenten

6

Edukt 3

HCID 516892Sodium Bicarbonate2×HCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chlorideHCID 21055240(1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

Produkt 1

HCID 58612411{1-Benzyl-2-hydroxy-3-[isobutyl-(2-oxo-2,3-dihydro-1H-indole-5-sulfonyl)-amino]-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl esterAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (1-benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 19 (59 mg, 0.15 mmol) in CH2Cl2 (1.6 ml) was added saturated aqueous sodium bicarbonate (0.4 ml), solid sodium bicarbonate (16 mg, 0.19 mmol), and then 2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride 14 (42 mg, 0.18 mmol). The mixture was stirred overnight, diluted with ethyl acetate, washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide the title product as a white solid, (79 mg, 90%). TLC: Rf 0.33 (Ethyl acetate). MS m/z 588 (MH)+. 1H NMR (CDCl3) is consistent with the structure.

Aufarbeitung

  1. washwashed with saturated brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9f74c7cdf5a34a7086ebad7cc362527b
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807845B2

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