Thiourea → HCID 131713975, compound

HRID 1153778Notes

Reaction equation

ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:43][O:44][CH2:45][CH3:46])[C:12]([NH:14][CH:15]2[C:41](=[O:42])[N:17]3[C:18]([C:25]([O:27][CH:28]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])=[C:19]([CH2:22][O:23][CH3:24])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1)=O.NC(N)=S>>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:43][O:44][CH2:45][CH3:46])[C:12]([NH:14][CH:15]2[C:41](=[O:42])[N:17]3[C:18]([C:25]([O:27][CH:28]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])=[C:19]([CH2:22][O:23][CH3:24])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1

Participants

Reactant 2

HCID 2723790Thiourea

HCID 131713974HCID 131713974, compound

Product 1

HCID 131713975HCID 131713975, compoundYield 69%

Procedure

191 mg of this benzhydryl 7-[2-(2-chloroacetamidothiazol-4-yl)-2-ethoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylate were then treated with 40 mg of thiourea, as described in Preparation 4, to give 117 mg of benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-ethoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylate, in the form of a pale pink powder, which was then treated with 1.5 ml of trifluoroacetic acid in a mixture of anisole and methylene chloride. When diisopropyl ether was added to the mixture, a precipitate was obtained and this was collected by filtration, to give 90 mg of 7-[2-(2-aminothiazol-4-yl)-2-ethoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylic acid trifluoroacetate.

Workup

customas described in Preparation 4

Sources & evidence

ORD record: ord-ad968d911fb348bd9e4e39be1af55f47
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04486425

Reaction notes

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