N-Methyl-D-glucamine → HCID 178484186, compound

HRID 846887Notes

Reaction equation

HRID 846887 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:38]/[O:39][CH2:40][S:41]([C:44]2[CH:49]=[CH:48][C:47]([OH:50])=[C:46]([OH:51])[CH:45]=2)(=[O:43])=[O:42])/[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[S:13][CH2:14][C:15]([CH2:23][S:24][C:25]2[N:30]4[N:31]=[C:32]([C:34](=[O:36])[NH2:35])[N:33]=[C:29]4[N:28]=[C:27]([CH3:37])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.[CH3:52][NH:53][CH2:54][C@@H:55]([C@H:57]([C@@H:59]([C@@H:61]([CH2:63][OH:64])[OH:62])[OH:60])[OH:58])[OH:56]>O>[CH3:52][NH:53][CH2:54][C@@H:55]([C@H:57]([C@@H:59]([C@@H:61]([CH2:63][OH:64])[OH:62])[OH:60])[OH:58])[OH:56].[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:38]/[O:39][CH2:40][S:41]([C:44]2[CH:49]=[CH:48][C:47]([OH:50])=[C:46]([OH:51])[CH:45]=2)(=[O:42])=[O:43])/[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[S:13][CH2:14][C:15]([CH2:23][S:24][C:25]2[N:30]4[N:31]=[C:32]([C:34](=[O:36])[NH2:35])[N:33]=[C:29]4[N:28]=[C:27]([CH3:37])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 8567N-Methyl-D-glucamineHCID 88442776(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(3,4-dihydroxyphenyl)sulfonylmethoxyimino]acetyl]amino]-3-[(2-carbamoyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 178484186HCID 178484186, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 373 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[[(3,4-dihydroxyphenyl)sulphonyl]methoxy]imino]acetamido]-3-[[(2-carbamoyl-5-methyl-s-triazolo-[1,5-a]pyrimidin-7-yl)-thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid in 7 ml of water was treated portionwise while stirring with 91 mg of N-methyl-D-glucamine. The resulting clear solution was lyophilized. There was obtained (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[[(3,4-dihydroxyphenyl)sulphonyl]methoxy]imino]acetamido]-3-[[(2-carbamoyl-5-methyl-s-triazolo-[1,5-a]pyrimidin-7-yl)-thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-methyl-D-glucamine salt as a white powder.

Workup

  1. additionwas treated portionwise

Sources & evidence

ORD record
ord-69f0da9d52c24242ab73ba719c3dc890
Source dataset
uspto-grants-1992_08
Patent number
US05138066

Reaction notes

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