Formaldehyde → HCID 131711774, compound

HRID 1395778Notes

Reaction equation

HRID 1395778 reaction equation
[CH3:1][CH2:2][C:3]([NH:5][CH:6]1[C:25](=[O:26])[N:8]2[C:9]([C:22]([OH:24])=[O:23])=[C:10]([CH2:13][S:14][C:15]3[S:16][C:17]([CH2:20][NH2:21])=[N:18][N:19]=3)[CH2:11][S:12][C@H:7]12)=[S:4].[OH-].[Na+:28].[S:29](=[O:32])([OH:31])[O-:30].[Na+].[CH2:34]=O>O>[CH3:1][CH2:2][C:3]([NH:5][CH:6]1[C:25](=[O:26])[N:8]2[C:9]([C:22]([O-:24])=[O:23])=[C:10]([CH2:13][S:14][C:15]3[S:16][C:17]([CH2:20][NH:21][CH2:34][S:29]([OH:31])(=[O:30])=[O:32])=[N:18][N:19]=3)[CH2:11][S:12][C@H:7]12)=[S:4].[Na+:28].[Na+:28].[CH3:1][CH2:2][C:3]([NH:5][CH:6]1[C:25](=[O:26])[N:8]2[C:9]([C:22]([O-:24])=[O:23])=[C:10]([CH2:13][S:14][C:15]3[S:16][C:17]([CH2:20][NH:21][CH2:34][S:29]([OH:31])(=[O:30])=[O:32])=[N:18][N:19]=3)[CH2:11][S:12][C@H:7]12)=[S:4]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 23665763Sodium BisulfiteHCID 131711043HCID 131711043, compound

Product 1

HCID 131711774HCID 131711774, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
60 °C

Procedure

To a suspension of 7-(2-methylthioacetamido)-3-(5-aminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (4.05 g.) in water (20 ml.) was added 1 N aqueous sodium hydroxide solution (9 ml.) under ice cooling to dissolve. Sodium bisulfite (3.12 g.) and 39% formaldehyde (2.25 ml.) were added to water (7.5 ml.) and, the solution was warmed at 60° C. for 5 minutes and adjusted to the total amount of 50 ml. by water. Thus obtained solution (22.5 ml.) was added to the solution above prepared all at once. The mixed solution was stirred at room temperature for 2 hours, and an insoluble product was filtered off and then the filtrate was concentrated under reduced pressure. The residue was dissolved in water (10 ml.) and purified on a column of an adsorption resin (Amberlite XAD-2: made by Rohm & Haas Co.) to give di-sodium 7-(2-methylthioacetamido)-3-(5-sulfomethylaminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylate (983 mg.) m.p. 145° to 150° C. (dec.).

Workup

  1. dissolutionto dissolve
  2. additionThus obtained solution (22.5 ml.) was added to the solution
  3. customabove prepared all at once
  4. filtrationan insoluble product was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in water (10 ml.)
  7. custompurified on a column of an adsorption resin (Amberlite XAD-2: made by Rohm & Haas Co.)

Sources & evidence

ORD record
ord-cd8ef3fe9d0a4eeb8cd1d1331c6d234e
Source dataset
uspto-grants-1980_05
Patent number
US04205166

Reaction notes

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