Sodium Hydroxide → HCID 178499047, compound

HRID 1087434Notes

Reaction equation

HRID 1087434 reaction equation
[NH2:1][O:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([OH:14])[C:10](=[CH:12][CH:13]=1)[OH:11])(=[O:6])=[O:5].[NH2:15][C:16]1[S:17][CH:18]=[C:19]([C:21](=O)[C:22]([NH:24][C@@H:25]2[C:32](=[O:33])[N:31]3[C@@H:26]2[S:27][CH2:28][C:29]([CH2:37][S:38][C:39]2[N:44]4[N:45]=[C:46]([C:48]([O:50][CH3:51])=[O:49])[N:47]=[C:43]4[N:42]=[C:41]([CH3:52])[CH:40]=2)=[C:30]3[C:34]([OH:36])=[O:35])=[O:23])[N:20]=1.[OH-].[Na+:55].O.CO>O.CO>[Na+:55].[NH2:15][C:16]1[S:17][CH:18]=[C:19](/[C:21](=[N:1]/[O:2][CH2:3][S:4]([C:7]2[CH:13]=[CH:12][C:10]([OH:11])=[C:9]([OH:14])[CH:8]=2)(=[O:5])=[O:6])/[C:22]([NH:24][C@@H:25]2[C:32](=[O:33])[N:31]3[C@@H:26]2[S:27][CH2:28][C:29]([CH2:37][S:38][C:39]2[N:44]4[N:45]=[C:46]([C:48]([O:50][CH3:51])=[O:49])[N:47]=[C:43]4[N:42]=[C:41]([CH3:52])[CH:40]=2)=[C:30]3[C:34]([O-:36])=[O:35])=[O:23])[N:20]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 19022435HCID 19022435, compoundHCID 22242641Methanol--water (1/1)HCID 88442830HCID 88442830, compound

Product 1

HCID 178499047HCID 178499047, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

122 mg of 4-[[(aminooxy)methyl]sulphonyl]pyrocatechol were reacted with 236 mg of (6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[[2-(methoxycarbonyl)-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 according to the procedure described in Example 7. The crude product obtained was suspended in 10 ml of water and brought into solution by the slow addition of 0.1N sodium hydroxide solution, with care being taken that the pH of the solution did not exceed 7. By chromatography on MCI gel CHP 2OP using water as the elution agent as well as water/methanol mixtures with increasing amounts of methanol and lyophilization of the concentrated product fractions, there was obtained (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[[(3,4-dihydroxyphenyl)sulphonyl]methoxy]imino]acetamido]-3-[[(2-(methoxycarbonyl)-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 monosodium salt as a white powder.

Workup

  1. customThe crude product obtained

Sources & evidence

ORD record
ord-a0e7de350d4247aeb24b7daa4246696c
Source dataset
uspto-grants-1991_07
Patent number
US05036064

Reaction notes

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