Sodium Hydroxide → HCID 178481956, compound

HRID 1461055Notes

Reaction equation

HRID 1461055 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:12][O:13]/[N:14]=[C:15](/[C:19]2[N:20]=[C:21]([NH2:24])[S:22][CH:23]=2)\[C:16]([OH:18])=[O:17])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[OH:8].[NH2:25][C@@H:26]1[C:33](=[O:34])[N:32]2[C@@H:27]1[S:28][CH2:29][C:30]([CH2:38][S:39][C:40]1[N:41]([CH3:48])[N:42]=[C:43]([OH:47])[C:44](=[O:46])[N:45]=1)=[C:31]2[C:35]([OH:37])=[O:36].[OH-].[Na+:50]>>[Na+:50].[Na+:50].[NH2:24][C:21]1[S:22][CH:23]=[C:19](/[C:15](=[N:14]/[O:13][CH2:12][S:9]([C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=2)(=[O:10])=[O:11])/[C:16]([NH:25][C@@H:26]2[C:33](=[O:34])[N:32]3[C@@H:27]2[S:28][CH2:29][C:30]([CH2:38][S:39][C:40]2[N:41]([CH3:48])[N:42]=[C:43]([OH:47])[C:44](=[O:46])[N:45]=2)=[C:31]3[C:35]([O-:37])=[O:36])=[O:18])[N:20]=1.[NH2:24][C:21]1[S:22][CH:23]=[C:19](/[C:15](=[N:14]/[O:13][CH2:12][S:9]([C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=2)(=[O:10])=[O:11])/[C:16]([NH:25][C@@H:26]2[C:33](=[O:34])[N:32]3[C@@H:27]2[S:28][CH2:29][C:30]([CH2:38][S:39][C:40]2[N:41]([CH3:48])[N:42]=[C:43]([OH:47])[C:44](=[O:46])[N:45]=2)=[C:31]3[C:35]([O-:37])=[O:36])=[O:17])[N:20]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 88625979HCID 88625979, compoundHCID 178481955HCID 178481955, compound

Product 1

HCID 178481956HCID 178481956, compound

Procedure

37 mg of 2-amino-4-thiazoleglyoxylic acid (Z)-O-[[(3,4-dihydroxyphenyl)-sulphonyl]methyl] oxime were reacted with 47 mg of (6R,7R)-7-amino-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-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 5. The product fractions obtained upon chromatography on MCI gel according to the method described in Example 1 were concentrated and the pH of solution thus obtained was adjusted to 7 with dilute sodium hydroxide solution. By lyophilization, there was obtained (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[[(3,4-dihydroxyphenyl)sulphonyl]methoxy]imino]acetamido]-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid disodium salt as a pale yellow powder.

Workup

  1. customThe product fractions obtained upon chromatography on MCI gel
  2. concentrationwere concentrated
  3. customthe pH of solution thus obtained

Sources & evidence

ORD record
ord-accf2e8b8bb047199ec08864ff66dd81
Source dataset
uspto-grants-1991_12
Patent number
US05073550

Reaction notes

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