Hydrochloric Acid → 7-(2-Methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid

HRID 463402Notes

Reaction equation

HRID 463402 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C.[CH3:21][O:22][N:23]=[C:24]([C:41](=[O:43])[CH3:42])[C:25]([NH:27][CH:28]1[C:39](=[O:40])[N:30]2[CH:31]([C:36]([OH:38])=[O:37])[CH:32](O)[CH2:33][S:34][C@H:29]12)=[O:26].Cl>O1CCCC1.O.C(OCC)(=O)C>[CH3:21][O:22][N:23]=[C:24]([C:41](=[O:43])[CH3:42])[C:25]([NH:27][CH:28]1[C:39](=[O:40])[N:30]2[C:31]([C:36]([OH:38])=[O:37])=[CH:32][CH2:33][S:34][C@H:29]12)=[O:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 867380887-(2-Methoxyimino-3-oxobutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 1317125287-(2-Methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acidYield 69.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroaceticanhydride (0.2 ml.) and triethylamine (0.12 ml.) were added to a solution of 7-(2-methoxyimino-3-oxobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 100 mg.) in dry tetrahydrofuran (10 ml.), and allowed to stand at room temperature for 10 minutes. Ethyl acetate (30 ml.) and water (10 ml.) were added to the reaction mixture and adjusted to pH 2 with hydrochloric acid. The ethyl acetate layer was separated, washed with water, dried over magnesium sulfate and then evaporated in vacuo. The residue was crystallized with diethyl ether to give 7-(2-methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 66 mg.).

Workup

  1. customThe ethyl acetate layer was separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized with diethyl ether

Sources & evidence

ORD record
ord-733abb4717f84a9c9736a19ec86e10b5
Source dataset
uspto-grants-1985_05
Patent number
US04518774

Reaction notes

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