7-Aminocephalosporanic acid → HCID 178476912, compound

HRID 1763469Notes

Reaction equation

HRID 1763469 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.[CH2:19]([O:21][P:22]([CH2:27][N:28]1[C:32]([SH:33])=[N:31][N:30]=[N:29]1)([O:24][CH2:25][CH3:26])=[O:23])[CH3:20].[P:34]([CH2:38][N:39]1[C:43]([SH:44])=[N:42][N:41]=[N:40]1)([OH:37])([OH:36])=[O:35].C(=O)(O)[O-].[Na+]>>[NH2:13][C@@H:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH:5]([S:44][C:43]3[NH:42][N:41]=[N:40][N:39]=3)[CH2:27][P:22]([O:21][CH2:19][CH3:20])([O:24][CH2:25][CH3:26])=[O:23])[CH2:15][S:14][C@H:9]12.[NH2:13][C@@H:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH:5]([CH2:38][P:34]([OH:37])([OH:36])=[O:35])[S:33][C:32]3[NH:28][N:29]=[N:30][N:31]=3)[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 4

HCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178476915HCID 178476915, compoundHCID 178527083HCID 178527083, compound

Product 2

HCID 178476912HCID 178476912, compoundHCID 178511755HCID 178511755, compound

Procedure

Reaction of 7-aminocephalosporanic acid with 1-diethoxyphosphinylmethyltetrazole-5-thiol and 1-phosphonomethyltetrazole-5-thiol in the presence of 1 and 3 molecular equivalents of sodium bicarbonate, respectively, as described in Example 10 gives 7β-amino-3-(1-diethoxyphosphinylmethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid and 7β-amino-3-(1-phosphono-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid, respectively.

Sources & evidence

ORD record
ord-f1e05e89c7584b18babcf5e4fb76e81f
Source dataset
uspto-grants-1978_09
Patent number
US04112086

Reaction notes

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