N-Methyl-D-glucamine → 1-deoxy-1-[{[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)phenyl]sulfonyl}(methyl)amino]-D-glucitol

HRID 1025469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1025469
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:41]=[CH:42][CH:43]=1)[C:8]([NH:10][C:11]1[S:12][C:13]2[CH2:40][CH2:39][CH2:38][CH2:37][C:14]=2[C:15]=1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)=[O:17])=[O:9])(=[O:4])=[O:3].[CH3:44][NH:45][CH2:46][C@@H:47]([C@H:49]([C@@H:51]([C@@H:53]([CH2:55][OH:56])[OH:54])[OH:52])[OH:50])[OH:48]>ClCCl>[CH3:34][O:33][C:31]([C:30]1[CH:35]=[CH:36][C:27]([CH2:26][CH2:25][C:22]2[CH:23]=[CH:24][C:19]([NH:18][C:16]([C:15]3[C:14]4[CH2:37][CH2:38][CH2:39][CH2:40][C:13]=4[S:12][C:11]=3[NH:10][C:8]([C:7]3[CH:6]=[C:5]([S:2]([N:45]([CH3:44])[CH2:46][C@@H:47]([C@H:49]([C@@H:51]([C@@H:53]([CH2:55][OH:56])[OH:54])[OH:52])[OH:50])[OH:48])(=[O:4])=[O:3])[CH:43]=[CH:42][CH:41]=3)=[O:9])=[O:17])=[CH:20][CH:21]=2)=[CH:28][CH:29]=1)=[O:32]

Komponenten

4

Edukt 2

HCID 8567N-Methyl-D-glucamineHCID 86676332Methyl 4-[2-(4-{[(2-{[3-(chlorosulfonyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate

Produkt 1

HCID 712440511-deoxy-1-[{[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)phenyl]sulfonyl}(methyl)amino]-D-glucitolAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 250 mg of methyl 4-[2-(4-{[(2-{[3-(chlorosulfonyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate, 153 mg of N-methyl-D-glucamine, and 2.5 mL of dichloromethane was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was washed with water to obtain 256 mg of 1-deoxy-1-[{[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)phenyl]sulfonyl}(methyl)amino]-D-glucitol as a yellow solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe residue was washed with water

Quellen und Nachweise

ORD-Eintrag
ord-212f844402d44416943027a1726a2b67
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729068B2

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