Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1) → Diphenylmethyl 7-(2-thienylacetamido)-3-(2-carbethoxymethylhydrazono)methyl-3-cephem-4-carboxylate

HRID 866869Notes

Reaction equation

HRID 866869 reaction equation
[CH:1]([C:3]1[CH2:4][S:5][C@@H:6]2[CH:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=O.Cl.[C:38]([CH2:43][NH:44][NH2:45])([O:40][CH2:41][CH3:42])=[O:39]>O1CCCC1.O>[S:31]1[CH:32]=[CH:33][CH:34]=[C:30]1[CH2:29][C:28]([NH:27][CH:26]1[C:25](=[O:36])[N:7]2[C:8]([C:9]([O:11][CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:10])=[C:3]([CH:1]=[N:45][NH:44][CH2:43][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:4][S:5][C@H:6]12)=[O:35]

Participants

5

Reactant 2

HCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)HCID 88776158Diphenylmethyl 3-formyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate

Product 1

HCID 131711156Diphenylmethyl 7-(2-thienylacetamido)-3-(2-carbethoxymethylhydrazono)methyl-3-cephem-4-carboxylateYield 69.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diphenylmethyl 3-formyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate (155 mg) in tetrahydrofuran (15 ml) is added a solution of carbethoxymethylhydrazine hydrochloride (69 mg) in water (2.5 ml), and the mixture is kept at room temperature for 2 days. The crystals obtained by concentration of the reaction mixture are collected by filtration, washed with ether and water, and dried to give diphenylmethyl 7-(2-thienylacetamido)-3-(2-carbethoxymethylhydrazono)methyl-3-cephem-4-carboxylate (129 mg). m.p. 70°-75° C. Yield: 69%. IR: νmaxNujol 3270, 1780, 1745, 1670; 1540cm-1. NMR: δd 6-DMSO (60MHz) 1.435 (6Hz) 3H, 3.52ABq (24; 17Hz) 2H, 3.48s2H, 3.60s2H, 4.17 quintet (6Hz) 2H, 4.95d(5Hz)1H, 5.70dd(8;4Hz)1H, 6.67-7.63m16H, 8.03s1H. [ α]D24.5 - 144° (c=0.340, CHCl3).

Workup

  1. customThe crystals obtained by concentration of the reaction mixture
  2. filtrationare collected by filtration
  3. washwashed with ether and water
  4. customdried

Sources & evidence

ORD record
ord-0db527d6bd5243bc981fb1107a25707d
Source dataset
uspto-grants-1978_07
Patent number
US04101658

Reaction notes

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