Hydrochloric Acid → HCID 70504870, compound

HRID 1463137Notes

Reaction equation

HRID 1463137 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([NH:10][CH:11]1[C:39](=[O:40])[N:13]2[CH:14]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:15]([CH2:19][O:20]C=O)=[C:16]([CH3:18])[S:17][C@H:12]12)=[O:9].CCOC(C)=O.O>CN(C=O)C>[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([NH:10][CH:11]1[C:39](=[O:40])[N:13]2[CH:14]([C:23]([O:25][CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:24])[C:15]([CH2:19][OH:20])=[C:16]([CH3:18])[S:17][C@H:12]12)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 88716747HCID 88716747, compound

Product 1

HCID 70504870HCID 70504870, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 22.8 ml portion of 2N HCl was added to a solution of 30 g of diphenylmethyl 7-(2-thienylacetamido)-2-methyl-3-formyloxymethylceph-2-em-4-carboxylate in 100 ml of DMF, and the mixture was stirred at room temperature for 20 hours. AcOEt and H2O were added to the reaction solution to separate out the AcOEt layer. The AcOEt layer was washed with 5% aqueous NaHCO3 solution and with saturated aqueous NaCl solution, and dried over Na2SO4, followed by distilling off the AcOEt under reduced pressure. The residue was added on a column of silica gel and washed with CH2Cl2.AcOEt (10:1). Then, the fractions eluted with acetone were collected, and the solvent was distilled off under reduced pressure, resulting 14.6 g (62%) of diphenylmethyl 7-(2-thienylacetamido)-2-methyl-3-hydroxymethylceph-2-em-4-carboxylate.

Workup

  1. customto separate out the AcOEt layer
  2. washThe AcOEt layer was washed with 5% aqueous NaHCO3 solution and with saturated aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. distillationby distilling off the AcOEt under reduced pressure
  5. additionThe residue was added on a column of silica gel
  6. washwashed with CH2Cl2
  7. washThen, the fractions eluted with acetone
  8. customwere collected
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6fc685db410c4bd58a3d91a83eb4707a
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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