3-Acetoxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid → 3-Acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-vinyloxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

HRID 2049175Notes

Reaction equation

HRID 2049175 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:29])[C:19]([C:23]3[N:24]=[C:25]([NH2:28])[S:26][CH:27]=3)=[N:20][O:21]C)[C:15](=[O:30])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(OCC1CS[C@@H]2C(NC(=O)C(C3N=C(N)SC=3)=NOC)C(=O)N2C=1C([O-])=O)(=O)C.[Na+].[C:62]([O:65][CH2:66][C:67]1[CH2:68][S:69][C@@H:70]2[CH:77]([NH:78][C:79](=[O:92])[C:80]([C:86]3[N:87]=[C:88]([NH2:91])[S:89][CH:90]=3)=[N:81][O:82][CH:83](C)[CH3:84])[C:76](=[O:93])[N:71]2[C:72]=1[C:73]([OH:75])=[O:74])(=[O:64])[CH3:63]>>[NH2:28][C:25]1[S:26][CH:27]=[C:23]([C:19](=[N:20][OH:21])[C:18]([NH:17][CH:16]2[C:15](=[O:30])[N:10]3[C:11]([C:12]([OH:14])=[O:13])=[C:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH2:7][S:8][C@H:9]23)=[O:29])[N:24]=1.[C:62]([O:65][CH2:66][C:67]1[CH2:68][S:69][C@@H:70]2[CH:77]([NH:78][C:79](=[O:92])[C:80]([C:86]3[N:87]=[C:88]([NH2:91])[S:89][CH:90]=3)=[N:81][O:82][CH:83]=[CH2:84])[C:76](=[O:93])[N:71]2[C:72]=1[C:73]([OH:75])=[O:74])(=[O:64])[CH3:63]

Participants

5

Reactant 3

HCID 1317115033-Acetoxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acidHCID 1317115073-Acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-(1-methylethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acidHCID 131711736Sodium 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylate

Product 2

HCID 1317117343-Acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-vinyloxyimino-acetamido]-ceph-3-eme-4-carboxylic acidHCID 1317117353-Acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Procedure

Gelules were prepared with 250 mg of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid or sodium 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylate or 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-(1-methylethoxylimino)-acetamido]-ceph-3-eme-4-carboxylic acid or the syn isomer of 7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-3-acetoxymethyl-ceph-3-eme-4-carboxylic acid or the syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-vinyloxyimino-acetamido]-ceph-3-eme-4-carboxylic acid and sufficient excipient to obtain a final weight of 400 mg.

Sources & evidence

ORD record
ord-d1d87e245b824776afff77e8ce2ffd55
Source dataset
uspto-grants-1980_04
Patent number
US04196205

Reaction notes

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