Water → HCID 54237243, compound

HRID 1660380Notes

Reaction equation

C([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH:25]=[CH:26][S:27][CH3:28])[CH:20]([NH:29][C:30](=[O:60])[C:31](=[N:57][O:58][CH3:59])[C:32]1[N:33]=[C:34]([NH:37]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:35][CH:36]=1)[C:19]2=[O:61])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.O>C(O)=O>[NH2:37][C:34]1[S:35][CH:36]=[C:32]([C:31](=[N:57][O:58][CH3:59])[C:30]([NH:29][CH:20]2[C:19](=[O:61])[N:18]3[CH:21]2[S:22][CH2:23][C:24]([CH:25]=[CH:26][S:27][CH3:28])=[C:17]3[C:15]([OH:16])=[O:14])=[O:60])[N:33]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylamino-thiazol-4-yl)-acetamido]-3-(2-methylthiovinyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (syn isomer, mixture of E- and Z-forms) (1.26 g) is dissolved in formic acid (35 cc), water (13 cc) is added and the mixture is heated at 50° C. for 15 minutes. It is then allowed to cool, filtered and concentrated to dryness under reduced pressure (20 mm Hg at 20° C.). The residue is triturated in diethyl ether (20 cc), filtered off, washed with ether (20 cc) and dried. 7-[2-(2-Aminothiazol-4-yl)-2-methoxyimino-acetamido]-2-carboxy-3-(2-methylthio-vinyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (syn isomer, mixture of E- and Z-forms) (0.63 g) is obtained as a solvate with formic acid, in the form of a cream-coloured powder.

Workup

temperatureto cool
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure (20 mm Hg at 20° C.)
customThe residue is triturated in diethyl ether (20 cc)
filtrationfiltered off
washwashed with ether (20 cc)
customdried

Sources & evidence

ORD record: ord-c7f6ea8cd2f2464c819a518f9b192371
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04307233

Reaction notes

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