7-Aminocephalosporanic acid → HCID 70589106, compound

HRID 2049568Notes

Reaction equation

HRID 2049568 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.[SH:19][C:20]1[S:24][C:23]([CH2:25][C:26]([NH2:28])=[O:27])=[N:22][N:21]=1>>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:19][C:20]3[S:24][C:23]([CH2:25][C:26](=[O:27])[NH2:28])=[N:22][N:21]=3)[CH2:15][S:14][C@H:9]12

Participants

3

Reactant 2

HCID 4413287-Aminocephalosporanic acidHCID 178513878HCID 178513878, compound

Product 1

HCID 70589106HCID 70589106, compoundYield 69.8%

Procedure

7-ACA and 5-mercapto-1,3,4-thiadiazol-2-ylacetamide were reacted as described in example 23a to give the title compound in 69.8% yield; δ(CF3CO2H) 3.93 (2H,s, C2 methylene), 4.63 (2H,s, --CH2CO--), 4.82 (2H,bs, --CH2S--), 5.47 (2H,s, β-lactam protons), 7.2-7.8 (2H,m, --CONH2).

Sources & evidence

ORD record
ord-3a2c65dd25b148a4b7dae85dc3ce734f
Source dataset
uspto-grants-1980_04
Patent number
US04198406

Reaction notes

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