2-(3-Methyl-1,2,4-oxadiazol-5-yl)acetic acid → Cephalosporanic Acid

HRID 971712Notes

Reaction equation

HRID 971712 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[O:4][N:3]=1.[NH2:11][CH:12]1[C:30](=[O:31])[N:14]2[C:15]([C:27]([OH:29])=[O:28])=[C:16]([CH:19]([C:21]3[N:25]([CH3:26])[N:24]=[N:23][N:22]=3)[SH:20])[CH2:17][S:18][C@H:13]12>C(#N)C.C(N1C=CN=C1)=C>[CH3:1][C:2]1[N:6]=[C:5]([CH2:7][C:8]([NH:11][CH:12]2[C:30](=[O:31])[N:14]3[C:15]([C:27]([OH:29])=[O:28])=[C:16]([CH:19]([C:21]4[N:25]([CH3:26])[N:24]=[N:23][N:22]=4)[SH:20])[CH2:17][S:18][C@H:13]23)=[O:10])[O:4][N:3]=1.[CH3:7][C:8]([O:10][CH2:19][C:16]1[CH2:17][S:18][C@@H:13]2[CH2:12][C:30](=[O:31])[N:14]2[C:15]=1[C:27]([OH:29])=[O:28])=[O:9]

Participants

6

Reactant 2

HCID 213130182-(3-Methyl-1,2,4-oxadiazol-5-yl)acetic acidHCID 887965197-Amino-3-(1-methyltetrazol-5-yl-mercaptomethyl)-3-cephem-4-carboxylic acid

Product 2

HCID 12302722Cephalosporanic AcidHCID 887964897-[3-Methyl-1,2,4-oxadiazol-5-yl-acetamido]-3-[1-methyltetrazol-5-yl-mercaptomethyl]-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 661711-VinylimidazoleSolvent

Procedure

Using the same procedure, 4 mmol of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid and 4 mmol of 7-amino-3-(1-methyltetrazol-5-yl-mercaptomethyl)-3-cephem-4-carboxylic acid (90% purity) in 35 ml of dry acetonitrile and 0.1 ml of N-vinyl-imidazole were reacted for one hour at room temperature and two hours at 50° C. to obtain a 37% yield of almost pure 7-[3-methyl-1,2,4-oxadiazol-5-yl-acetamido]-3-[1-methyltetrazol-5-yl-mercaptomethyl]-3-cephem-4-carboxylic acid with a 41% recovery of the starting cephalosporanic acid.

Workup

  1. customwere reacted for one hour at room temperature and two hours at 50° C.

Sources & evidence

ORD record
ord-d539a7b256794b43adf0ee3599d4d486
Source dataset
uspto-grants-1979_07
Patent number
US04160829

Reaction notes

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