7-Aminocephalosporanic acid → HCID 178485836, compound

HRID 435940Notes

Reaction equation

CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.C(OC([NH:26][CH:27]([C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38]([NH:40][CH3:41])=[O:39])=[CH:33][CH:32]=1)[C:28]([OH:30])=O)=O)(C)(C)C.[SH:42][C:43]1[N:44]=[N:45][NH:46][CH:47]=1>>[NH2:26][CH:27]([C:31]1[CH:32]=[CH:33][C:34]([NH:37][C:38]([NH:40][CH3:41])=[O:39])=[CH:35][CH:36]=1)[C:28]([NH:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:42][C:43]3[N:44]=[N:45][NH:46][CH:47]=3)[CH2:15][S:14][C@H:9]12)=[O:30]

Participants

Reactant 3

HCID 4413287-Aminocephalosporanic acid

HCID 20327942HCID 20327942, compound

HCID 178527738HCID 178527738, compound

Product 1

HCID 178485836HCID 178485836, compound

Procedure

Acylation of 7-ADCA, 7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid or any of the cephem compounds named in Example 6 with α-t-butoxycarboxyamino-p-(3-methylureido)phenylacetic acid followed by deblocking according to the procedure of Example 2 gives the corresponding 7-[α-amino-p-(3-methylureido)-phenyl-acetamido]cephem compound. 7-[α-amino-p-(3-methylureido) phenylacetamido]-3-(1,2,3-triazol-4-ylthiomethyl)-3-cephem-4-carboxylic acid is prepared by reacting 7-ACA with α-t-butoxycarbonylamino-p-(3-methylureido)phenylacetic acid and then with 4-mercapto-1,2,3-triazole with subsequent deblocking of the amino grouping according to the procedure of Example 5.

Sources & evidence

ORD record: ord-23fae46a3ba9431b969f688d996d58a9
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04007173

Reaction notes

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