Citric Acid → HCID 88716187, compound

HRID 1463148Notes

Reaction equation

HRID 1463148 reaction equation
N1C=CC=CC=1.[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][C:13]([NH:15][CH:16]1[C:42](=[O:43])[N:18]2[CH:19]([C:26]([O:28][CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])[C:20]([CH2:24][OH:25])=[C:21]([CH3:23])[S:22][C@H:17]12)=[O:14].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][C:13]([NH:15][CH:16]1[C:42](=[O:43])[N:18]2[CH:19]([C:26]([O:28][CH:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[O:27])[C:20]([CH:24]=[O:25])=[C:21]([CH3:23])[S:22][C@H:17]12)=[O:14]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 1049PyridineHCID 70504870HCID 70504870, compound

Product 1

HCID 88716187HCID 88716187, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 250 ml of CH2Cl2 containing 6.7 ml of pyridine at 20° C. was added 4.2 g of CrO3, and after stirring for 1 hour, a solution of 2.6 g of diphenylmethyl 7-(2-thienylacetamido)-2-methyl-3-hydroxymethylceph-2-em-4-carboxylate in 30 ml of CH2Cl2 was added to the mixture, followed by stirring vigorously for 5 minutes. 100 ml of 1M citric acid solution was added to the reaction solution, followed by stirring to separate out the CH2Cl2 layer. The CH2Cl2 layer was washed with H2O and saturated aqueous NaCl solution, successively, and dried over MgSO4, followed by distilling off the CH2Cl2 under reduced pressure. The residue was added on a column of silica gel, and the fractions eluted with CH2Cl2.ACOEt (20:1) were collected to distill off the solvent under reduced pressure, thus yielding 938 mg (36.2%) of diphenylmethyl 7-(2-thienylacetamido)-2-methyl-3-formylceph-2-em-4-carboxylate.

Workup

  1. stirringby stirring vigorously for 5 minutes
  2. stirringby stirring
  3. customto separate out the CH2Cl2 layer
  4. washThe CH2Cl2 layer was washed with H2O and saturated aqueous NaCl solution
  5. dry with materialsuccessively, and dried over MgSO4
  6. distillationby distilling off the CH2Cl2 under reduced pressure
  7. additionThe residue was added on a column of silica gel
  8. washthe fractions eluted with CH2Cl2
  9. customACOEt (20:1) were collected
  10. distillationto distill off the solvent under reduced pressure

Sources & evidence

ORD record
ord-03a6202bdec045ce8a9bbca53fb3c936
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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