Hydrochloric Acid → Diphenylmethyl 3-(sulfolan-3-ylhydrazono)methyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate

HRID 866870Notes

Reaction equation

HRID 866870 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.[S:37]1([CH2:43][CH2:42][CH:41]([NH:44][NH2:45])[CH2:40]1)(=[O:39])=[O:38].Cl>O1CCCC1.O>[S:37]1([CH2:43][CH2:42][CH:41]([NH:44][N:45]=[CH:1][C:3]2[CH2:4][S:5][C@@H:6]3[CH:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)[C:25](=[O:36])[N:7]3[C:8]=2[C:9]([O:11][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:10])[CH2:40]1)(=[O:39])=[O:38]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 103013(tetrahydro-3-thienyl)hydrazine S,S-dioxideHCID 88776158Diphenylmethyl 3-formyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate

Product 1

HCID 131711157Diphenylmethyl 3-(sulfolan-3-ylhydrazono)methyl-7-(2-thienylacetamido)-3-cephem-4-carboxylateYield 76%

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 (sulfolane-3-yl) hydrazine (70 mg) and 1.5 equivalents of hydrochloric acid in water (3 ml), and the mixture is kept at room temperature 5 hours. The crystals obtained by concentration of the reaction mixture are collected by filtration, washed with ether and water, and dried to give diphenylmethyl 3-(sulfolan-3-ylhydrazono)methyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate (142 mg). m.p. 117°-125° C. Yield: 76%. IR: νmaxNujol 3275, 1785, 1715, 1675, 1530cm-1.

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-5c1e8cdf36384d47b3c6054a3a4ccef1
Source dataset
uspto-grants-1978_07
Patent number
US04101658

Reaction notes

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