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 926080Notes

Reaction equation

HRID 926080 reaction equation
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]

Participants

4

Reactant 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

Product 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-glucitolYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-a35efa59ad934a04b431e82e3d371c9d
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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