Water → HCID 178509094, compound

HRID 1088649Notes

Reaction equation

C(=O)([O-])O.[Na+:5].[OH-].[Na+].O.Cl.[NH:10]=[C:11]1[NH:15][C:14]([C:16](=[N:44][OH:45])[C:17]([NH:19][CH:20]2[C:42](=[O:43])[N:22]3[C:23]([C:39]([OH:41])=[O:40])=[C:24]([CH2:27][O:28]C(=O)C(C4C=CC=CC=4)O)[CH2:25][S:26][C@H:21]23)=[O:18])=[CH:13][S:12]1>>[NH:10]=[C:11]1[NH:15][C:14]([C:16](=[N:44][OH:45])[C:17]([NH:19][CH:20]2[C:42](=[O:43])[N:22]3[C:23]([C:39]([O-:41])=[O:40])=[C:24]([CH2:27][OH:28])[CH2:25][S:26][C@H:21]23)=[O:18])=[CH:13][S:12]1.[Na+:5]

Participants

Reactant 4

HCID 962Water

HCID 14798Sodium Hydroxide

HCID 516892Sodium Bicarbonate

HCID 178479164HCID 178479164, compound

Product 1

HCID 178509094HCID 178509094, compound

Procedure

In 5 ml of there was dissolved 0.57 g of 7-[2-(2-imino-4-thiazolin-4-yl)-2-hydroxyimino-acetamido]-3-(mandelyloxymethyl)-3-cephem-4-carboxylic acid hydrochloride (syn-isomer) together with 0.17 g of sodium hydrogen carbonate and, while the mixed solution was stirred under ice-cooling, 0.55 ml of 2N-sodium hydroxide was added. The mixture was stirred at that temperature for 3 hours and, then, at room temperature for 1 hour. The reaction mixture was subjected to column chromatography on polystyrene resin (Amberlite XAD-2, Rohm and Haas Co.), development being carried out with water. The fractions containing the desired product were pooled and lyophilized. By the above procedure there was obtained 0.19 g of the captioned compound.

Workup

temperaturecooling
stirringThe mixture was stirred at that temperature for 3 hours

Sources & evidence

ORD record: ord-48113fd69d4b4ff989f553dc4464778d
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04963542

Reaction notes

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