Hydrochloric Acid → 7-(3-Ethoxycarbonylhydrazono-2-methoxyiminobutyramido)-3-cephem-4-carboxylic acid

HRID 1982040Notes

Reaction equation

HRID 1982040 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:14]([O:16][C:17]([NH:19][N:20]=[C:21]([CH3:42])[C:22](=[N:39][O:40][CH3:41])[C:23]([NH:25][CH:26]1[C:37](=[O:38])[N:28]2[CH:29]([C:34]([OH:36])=[O:35])[CH:30](O)[CH2:31][S:32][C@H:27]12)=[O:24])=[O:18])[CH3:15].[Cl-].[Na+].Cl>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:14]([O:16][C:17]([NH:19][N:20]=[C:21]([CH3:42])[C:22](=[N:39][O:40][CH3:41])[C:23]([NH:25][CH:26]1[C:37](=[O:38])[N:28]2[C:29]([C:34]([OH:36])=[O:35])=[CH:30][CH2:31][S:32][C@H:27]12)=[O:24])=[O:18])[CH3:15]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 9845Trifluoroacetic anhydrideHCID 867380897-(2-Methoxyimino-3-ethoxycarbonylhydrazonobutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 1317125327-(3-Ethoxycarbonylhydrazono-2-methoxyiminobutyramido)-3-cephem-4-carboxylic acidYield 93.4%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic anhydride (6.8 ml.) and triethylamine (4.2 ml.) were added to a solution of 7-(3-ethoxycarbonylhydrazono-2-methoxyiminobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 4.3 g.) in dry tetrahydrofuran (215 ml.) under ice cooling and stirred at the same temperature for an hour. To the resultant solution were added ethyl acetate (200 ml.) and a sodium chloride saturated aqueous solution (100 ml.), and adjusted to pH 2.0 with 6N hydrochloric acid. After separating the organic layer, the aqueous layer was extracted with ethyl acetate (100 ml.). The organic layer and the extract were combined; washed with a sodium chloride saturated aqueous solution and dried over magnesium sulfate. The solution was evaporated in vacuo, and diisopropyl ether (50 ml.) was added to the residue. The precipitates were collected by filtration and washed with diisopropyl ether to give 7-(3-ethoxycarbonylhydrazono-2-methoxyiminobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 3.85 g.).

Workup

  1. customAfter separating the organic layer
  2. extractionthe aqueous layer was extracted with ethyl acetate (100 ml.)
  3. washwashed with a sodium chloride saturated aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solution was evaporated in vacuo, and diisopropyl ether (50 ml.)
  6. additionwas added to the residue
  7. filtrationThe precipitates were collected by filtration
  8. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-b84cdc656f0f4a42985c91c0fbb05bcd
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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