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 1732883Notes

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-ff0dc1a046564e2c98dc693191657ac1
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04239758

Reaction notes

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