Water → HCID 136463161, compound

HRID 328069Notes

Reaction equation

HRID 328069 reaction equation
Cl.[NH2:2][C@@H:3]1[C:19](=[O:20])[N:5]2[C:6]([C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12])=[C:7]([CH3:10])[CH2:8][S:9][C@H:4]12.O.C(=O)(O)[O-].[Na+].[OH:27][C:28]1[C:35]([C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:34][C:31]([CH:32]=O)=[CH:30][C:29]=1[C:40]([CH3:43])([CH3:42])[CH3:41]>CO>[OH:27][C:28]1[C:35]([C:36]([CH3:38])([CH3:37])[CH3:39])=[CH:34][C:31]([CH:32]=[N:2][C@@H:3]2[C:19](=[O:20])[N:5]3[C:6]([C:11]([O:13][CH2:14][C:15]([Cl:16])([Cl:18])[Cl:17])=[O:12])=[C:7]([CH3:10])[CH2:8][S:9][C@H:4]23)=[CH:30][C:29]=1[C:40]([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 516892Sodium BicarbonateHCID 70622814HCID 70622814, compound

Product 1

HCID 136463161HCID 136463161, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 g. of 2,2,2-trichloroethyl 7β-amino-3-methyl-3-cephem-4-carboxylate hydrochloride was added about 70 ml. of water. About 2.5 g. of sodium bicarbonate was added thereto and, after stirring for a while, the resultant was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated at a temperature below 35° C. The so obtained free base was dissolved in 40 ml. of methanol and 5 g. of 4-hydroxy-3,5-di-tert.-butylbenzaldehyde was added thereto and stirring was continued at room temperature for 4 hours. The insolubles were dissolved by heating briefly and the reaction mixture was concentrated into a half amount thereof, which was then cooled to separate out crystalline substances. The substances were recovered by filtration and washed with cold methanol to give 2,2,2-trichloroethyl 7β-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)-3-methyl-3-cephem-4-carboxylate. Yield 7 g. The product was recrystallized from a small amount of methanol to give the pure product as slightly yellow colored crystals. m.p. 94° C.

Workup

  1. extractionthe resultant was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated at a temperature below 35° C
  4. customThe so obtained free base
  5. dissolutionwas dissolved in 40 ml
  6. stirringstirring
  7. dissolutionThe insolubles were dissolved
  8. temperatureby heating briefly
  9. concentrationthe reaction mixture was concentrated into a half amount
  10. temperaturewhich was then cooled
  11. customto separate out crystalline substances
  12. filtrationThe substances were recovered by filtration
  13. washwashed with cold methanol

Sources & evidence

ORD record
ord-6d5b76db6ffe4513922e0ed335ce06d8
Source dataset
uspto-grants-1977_04
Patent number
US04016155

Reaction notes

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