Hydrochloric Acid → HCID 88683839, compound

HRID 1164426Notes

Reaction equation

HRID 1164426 reaction equation
[OH:1][N:2]=[C:3]1[C:19](=[O:20])[N:5]2[C:6]([C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12])=[C:7]([CH3:10])[CH2:8][S:9][C@H:4]12.Cl>C(O)C.C(OCC)(=O)C>[OH:1][NH:2][C@@H:3]1[C:19](=[O:20])[N:5]2[C:6]([C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:16])[Cl:17])=[O:12])=[C:7]([CH3:10])[CH2:8][S:9][C@H:4]12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131712939HCID 131712939, compound

Product 1

HCID 88683839HCID 88683839, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In ethanol (0.6 ml) is dissolved 2,2,2-trichloroethyl 7-hydroxyimino-3-methyl-3-cephem-4-carboxylate (100 mg) and under ice-cooling, a solution of borane-pyridine complex (102 mg) in ethanol (0.7 ml) is added. Then, a 2 N-methanolic solution of hydrogen chloride (0.6 ml) is added dropwise in a nitrogen stream and the mixture is stirred at the same temperature for 3 hours. The mixture is further stirred at room temperature for an hour, after which time it is diluted with ethyl acetate, washed with water and aqueous sodium chloride in that order, dried over magnesium sulfate and concentrated under reduced pressure. The oily residue is subjected to silica gel (4.5 g) column chromatography and elution is carried out with ethyl acetate-hexane to give 2,2,2-trichloroethyl 7 β-hydroxyamino-3-methyl-3-cephem-4-carboxylate (79 mg) as an amorphous solid.

Workup

  1. temperatureunder ice-cooling
  2. stirringThe mixture is further stirred at room temperature for an hour
  3. washwashed with water and aqueous sodium chloride in that order
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe oily residue is subjected to silica gel (4.5 g) column chromatography and elution

Sources & evidence

ORD record
ord-8ac7ea60c6864fa2aaa298f6d49ee1d3
Source dataset
uspto-grants-1983_01
Patent number
US04369312

Reaction notes

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