Hydrochloric Acid → HCID 86744518, compound

HRID 704062Notes

Reaction equation

HRID 704062 reaction equation
[Cl-].[NH4+].[OH-].Br[CH2:5][CH:6]1[C@H:11]([C:12]([O:14][CH2:15][C:16](Cl)([Cl:18])[Cl:17])=[O:13])[N:10]2[C:20](=[O:32])[C@@H:21]([NH:22][C:23](=[O:31])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:9]2[S@@:8](=[O:33])[CH2:7]1.Cl>O.CC(C)=O.CN(C)C=O.[Zn]>[C:25]1([CH2:24][C:23]([NH:22][C@@H:21]2[C:20](=[O:32])[N:10]3[C@@H:11]([C:12]([O:14][CH2:15][CH:16]([Cl:17])[Cl:18])=[O:13])[C:6](=[CH2:5])[CH2:7][S@:8](=[O:33])[C@H:9]23)=[O:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 961HydroxideHCID 25517Ammonium ChlorideHCID 56626385HCID 56626385, compound

Product 1

HCID 86744518HCID 86744518, compoundYield 12.4%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

1.2 g (22.4 mmoles) of ammonium chloride in 2.2 ml of water and 1.2 ml of a 4N hydroxide solution at -10° C. were added to a stirred solution of 1.68 g (purity 92%; 2.78 mmoles) of trichloroethyl (1S,4R,6R,7R)-3-bromomethyl-1-oxo-7-phenylacetamidocepham-4-carboxylate in 15 ml of acetone and 2 ml of dimethylformamide. After adding 1.5 g (15.3 mmoles) of activated zinc powder the mixture was stirred at 4° C. for 70 min. Then 3 ml of water and 3.6 ml of a 4N hydrochloric acid solution were added and the solid material was filtered off. To the filtrate 50 ml of warm water was added. After cooling to 0° C. the crystals were filtered off, washed and dried giving 153 mg of dichloro-ethyl (1S,4R,6R,7R)-7-phenylacetamido-3-methylene-1-oxo-cepham-4-carboxylate with a purity of 83%. Yield 10%.

Workup

  1. filtrationthe solid material was filtered off
  2. additionTo the filtrate 50 ml of warm water was added
  3. temperatureAfter cooling to 0° C. the crystals
  4. filtrationwere filtered off
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-b022d41f4ebb4e2eb1d3aaf1305dbb1e
Source dataset
uspto-grants-1991_01
Patent number
US04985554

Reaction notes

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