Hydrochloric Acid → HCID 131711158, compound

HRID 866871Notes

Reaction equation

HRID 866871 reaction equation
[CH:1]([C:3]1[CH:8]([C:9]([O:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[N:7]2[C:25](=[O:36])[CH:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C@H:6]2[S:5][CH:4]=1)=O.[C:37]([NH:40][NH2:41])(=[O:39])[CH3:38].Cl>O1CCCC1.O>[C:37]([NH:40][N:41]=[CH:1][C:3]1[CH:8]([C:9]([O:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[N:7]2[C:25](=[O:36])[CH:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C@H:6]2[S:5][CH:4]=1)(=[O:39])[CH3:38]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14039AcetohydrazideHCID 88777142HCID 88777142, compound

Product 1

HCID 131711158HCID 131711158, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a procedure similar to that described in Example I-3, diphenylmethyl 3-formyl-7-(2-thienylacetamido)-2-cephem-4-carboxylate (104 mg) and acetylhydrazine (30 mg) are left to react in a mixture of tetrahydrofuran (8 ml) and water (1.5 ml) in the presence of hydrochloric acid (2 equivalents) at room temperature overnight to give diphenylmethyl 3-(2-acetylhydrazono)methyl-7-(2-thienylacetamido)-2-cephem-4-carboxylate (95 mg). m.p. 168-178° C (decomposition). Yield: 83%. IR: λmaxNujol 3280, 1760, 1743, 1695, 1667, 1697, 1677, 1538cm-1. UV: λmaxEtOH 301nm(ε=31700). NMR: δCDCl 3 (60MHz) 1.82s3H, 3.82s2H, 5.07d(4Hz)1H, 5.40s1H, 5.50br1H, 6.63br1H, 6.83s1H. 6.88-7.58m15-16H. [α]D23 +416° (c= 0.501, CHCl3).

Workup

  1. waitare left

Sources & evidence

ORD record
ord-7d3cafdd28c14a21b857635a38bab872
Source dataset
uspto-grants-1978_07
Patent number
US04101658

Reaction notes

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