Urea → p-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate

HRID 1657735Notes

Reaction equation

HRID 1657735 reaction equation
Cl.[NH2:2][CH:3]1[C:24](=[O:25])[N:5]2[C:6]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[O:12])=[C:7]([OH:10])[CH2:8][S:9][C@H:4]12.C(N(CC)CC)C.NC(N)=O.[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[CH2:42][C:43](Cl)=[O:44]>CC(C)=O>[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[CH2:42][C:43]([NH:2][CH:3]1[C:24](=[O:25])[N:5]2[C:6]([C:11]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=3)=[O:12])=[C:7]([OH:10])[CH2:8][S:9][C@H:4]12)=[O:44]

Participants

6

Reactant 4

HCID 1176UreaHCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 70559760p-Nitrobenzyl 7-amino-3-hydroxy-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 70559815p-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 1.55 g. of p-nitrobenzyl 7-amino-3-hydroxy-3-cephem-4-carboxylate hydrochloride in 30 ml. of acetone containing 364 mg. (0.5 ml., 3.6 mmole) of triethylamine was added 962 mg. of urea. With stirring at room temperature, a solution of 730 mg. (4.4 mmole) of 2-thiophene acetyl chloride in 20 ml. of acetone was added dropwise to the mixture. After 2.5 hours the reaction mixture was filtered and evaporated. The residue was dissolved in ethyl acetate and the solution was washed successively with water, a 5% solution of sodium bicarbonate, 5% hydrochloric acid, and a saturated solution of sodium chloride. The washed solution was dried and then was concentrated by evaporation in vacuo to yield 1.2 g. of the reaction product as a crystalline residue. The product was recrystallized from ethyl acetate to yield pure p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate having the following spectral properties.

Workup

  1. filtrationAfter 2.5 hours the reaction mixture was filtered
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed successively with water
  5. customThe washed solution was dried
  6. concentrationwas concentrated by evaporation in vacuo
  7. customto yield 1.2 g
  8. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fbdd3bf65d934d55a797e1d3a84785d5
Source dataset
uspto-grants-1976_06
Patent number
US03962227

Reaction notes

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