Hydrochloric Acid → Pivaloyloxymethyl 7-[(4-(3-aminopropyl)-1-piperidyl)-methyleneamino]-3-methyl-3-cephem-4-carboxylate, dihydrochloride

HRID 128210Notes

Reaction equation

HRID 128210 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH:13]=[N:14][CH:15]2[C:34](=[O:35])[N:17]3[C:18]([C:23]([O:25][CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[O:24])=[C:19]([CH3:22])[CH2:20][S:21][C@H:16]23)[CH2:9][CH2:8]1)=[N+]=[N-].O.[ClH:37]>C(OCC)(=O)C.[Pd]>[ClH:37].[ClH:37].[NH2:1][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH:13]=[N:14][CH:15]2[C:34](=[O:35])[N:17]3[C:18]([C:23]([O:25][CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:30])([CH3:31])[CH3:32])=[O:24])=[C:19]([CH3:22])[CH2:20][S:21][C@H:16]23)[CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 131712136Pivaloyloxymethyl 7-[(4-(3-azidopropyl)-1-piperidyl)-methyleneamino]-3-methyl-3-cephem-4-carboxylate

Product 1

HCID 131712137Pivaloyloxymethyl 7-[(4-(3-aminopropyl)-1-piperidyl)-methyleneamino]-3-methyl-3-cephem-4-carboxylate, dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of pivaloyloxymethyl 7-[(4-(3-azidopropyl)-1-piperidyl)-methyleneamino]-3-methyl-3-cephem-4-carboxylate (1.5 g) in ethyl acetate (25 ml) were added water (30 ml) and hydrochloric acid to pH=3. 10% palladium-on-carbon (0.5 g) was added, and hydrogen was bubbled through the stirred mixture, a pH-value of 3 being maintained by addition of 0.2 N hydrochloric acid. When the consumption of acid ceased, the catalyst was filtered off. The aqueous phase was separated and freeze-dried to yield the desired compound as an amorphous powder.

Workup

  1. customhydrogen was bubbled through the stirred mixture
  2. temperaturea pH-value of 3 being maintained by addition of 0.2 N hydrochloric acid
  3. customWhen the consumption of acid
  4. filtrationthe catalyst was filtered off
  5. customThe aqueous phase was separated
  6. customfreeze-dried

Sources & evidence

ORD record
ord-6aaf4f2dad0b4a2ba35360a3f0956e89
Source dataset
uspto-grants-1981_03
Patent number
US04259333

Reaction notes

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