7-Aminodeacetoxycephalosporanic acid → HCID 88628807, compound

HRID 652805Notes

Reaction equation

HRID 652805 reaction equation
CC(OCC1CS[C@@H]2[C@H](N)C(=O)N2C=1C(O)=O)=O.CC1CS[C@@H]2[C@H](N)C(=O)N2C=1C(O)=O.[NH2:33][CH:34]1[C:59](=[O:60])[N:36]2[C:37]([C:49]([O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[O:50])=[C:38]([O:41][S:42]([C:45]([F:48])([F:47])[F:46])(=[O:44])=[O:43])[CH2:39][CH2:40][C@H:35]12.[O:61]([CH2:68][C:69](Cl)=[O:70])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>C(#N)C.N1C=CC=CC=1.C(N(CC)CC)C>[O:61]([CH2:68][C:69]([NH:33][CH:34]1[C:59](=[O:60])[N:36]2[C:37]([C:49]([O:51][CH2:52][C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)=[O:50])=[C:38]([O:41][S:42]([C:45]([F:48])([F:47])[F:46])(=[O:44])=[O:43])[CH2:39][CH2:40][C@H:35]12)=[O:70])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1

Participants

8

Reactant 4

HCID 334987-Aminodeacetoxycephalosporanic acidHCID 69703Phenoxyacetyl chlorideHCID 4413287-Aminocephalosporanic acidHCID 88599689HCID 88599689, compound

Product 1

HCID 88628807HCID 88628807, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

The N-acylations are carried out by using the methods employed for the acylation of the cephalosporin nuclei such as 7-ACA and 7-ADCA. In an example of the acylation benzyl 7-amino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylate in acetonitrile is treated with phenoxyacetyl chloride in the presence of an acid-binding agent such as triethylamine or pyridine to provide benzyl 7-phenoxyacetylamino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylate.

Sources & evidence

ORD record
ord-1dfc1d035f4e483393eb913220bb37cd
Source dataset
uspto-grants-1987_06
Patent number
US04673737

Reaction notes

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