Hydrochloric Acid → (6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Reaction equation
C(O)C.[NH2:4][CH:5]1[C:26](=[O:27])[N:7]2[C:8]([C:13]([O:15]CC3C=CC([N+]([O-])=O)=CC=3)=[O:14])=[C:9]([CH3:12])[CH2:10][S:11][C@H:6]12.Cl>[Fe].O.CO>[NH2:4][CH:5]1[C:26](=[O:27])[N:7]2[C:8]([C:13]([OH:15])=[O:14])=[C:9]([CH3:12])[CH2:10][S:11][C@H:6]12Participants
Procedure
To a mixture of ethanol (120 ml) and water (25 ml), p-nitrobenzyl 7-amino-3-methyl-3-cephem-4-carboxylate (10 gm) was added. Iron powder (10 gm) was charged at 30° C., followed by the addition of concentrated HCl (12.5 ml) in a methanol (10 ml) and water (2.5 ml) mixture over a period of 15 minutes. The reaction mixture was stirred for 1 hour. After completion of the reaction, aq. KHCO3 was added to bring the pH to 8.0, followed by the addition of activated carbon. After stirring 10 minutes, the mixture was filtered. To the filtrate was added aq. HCl to bring the pH to 4.0. The product thus separated was filtered and dried to yield 4.3 gm (70.3%) of 7-amino-3-methyl-3-cephem-4-carboxylic acid as a white solid product. M.p. 217°-219° C.(d). IR(KBr) cm-1 3150, 1800, 1650, 1625, 1525, 1420, 1350, 790. NMR (D2O-DCl) δ :2.1 (s, 3 H,--CH3), 5.41(d, 1 H, S--CH), 5.86(m, 1 H, N--CH).
Workup
- additionwas added
- additionwas added
- additionfollowed by the addition of activated carbon
- stirringAfter stirring 10 minutes
- filtrationthe mixture was filtered
- additionTo the filtrate was added aq. HCl
- customThe product thus separated
- filtrationwas filtered
- customdried
Sources & evidence
- ORD record
- ord-ded5bd0df9434d55826af55a42fd3c03
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05536830
Reaction notes
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