Water → Sodium 7-[2-(2-imino-3-hydroxy-4-thiazolin-4-yl)acetamido]-3-(3-hydroxymethyl-4-methyl-1,2,4-triazol-5-yl)thiomethyl-3-cephem-4-carboxylate

HRID 427086Notes

Reaction equation

[NH:1]=[C:2]1[N:6]([OH:7])[C:5]([CH2:8][C:9]([NH:11][CH:12]2[C:27](=[O:28])[N:14]3[C:15]([C:24]([OH:26])=[O:25])=[C:16]([CH2:19]OC(=O)C)[CH2:17][S:18][C@H:13]23)=[O:10])=[CH:4][S:3]1.[OH:29][CH2:30][C:31]1[N:35]([CH3:36])[C:34]([SH:37])=[N:33][N:32]=1.C(=O)([O-])O.[Na+:42].O>P([O-])([O-])([O-])=O>[NH:1]=[C:2]1[N:6]([OH:7])[C:5]([CH2:8][C:9]([NH:11][CH:12]2[C:27](=[O:28])[N:14]3[C:15]([C:24]([O-:26])=[O:25])=[C:16]([CH2:19][S:37][C:34]4[N:35]([CH3:36])[C:31]([CH2:30][OH:29])=[N:32][N:33]=4)[CH2:17][S:18][C@H:13]23)=[O:10])=[CH:4][S:3]1.[Na+:42]

Participants

Conditions

Temperature: 70 °C

Procedure

In 20 ml of phosphate buffer (pH 6.4) is dissolved 1.0 g of 7-[2-(2-imino-3-hydroxy-4-thiazolin-4-yl)acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid together with 0.3 g of 3-hydroxymethyl-4-methyl-1,2,4-triazole-5-thiol and 0.336 g of sodium hydrogen carbonate and the solution is stirred at 70° C. for 2 hours . This reaction mixture is subjected to column chromatography on polystyrene resin (Amberlite XAD-2) with water as the developer and the fractions containing the contemplated product are pooled. This solution contains 3-hydroxymethyl-4-methyl-1,2,4-triazole-5-thiol together with the desired compound. The solution is lyophilized and the resultant powder is redissolved in water. The solution is then subjected to column chromatography on dextran gel (Sephadex LH-20®, Pharmacia) with water as the developer. The fractions containing the contemplated compound are pooled and lyophilized. By the above procedure is obtained the captioned compound. Yield 0.28 g.

Workup

additionthe fractions containing the contemplated product

Sources & evidence

ORD record: ord-08bbdc60533b425fafa3566fb5870a7d
Source dataset: uspto-grants-1979_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04172891

Reaction notes

Loading…