Trifluoroacetic acid → 1-Propionyloxyethyl 7-[2-carboxymethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylate

HRID 462600Notes

Reaction equation

HRID 462600 reaction equation
FC(F)(F)C(O)=O.C([O:21][C:22]([CH2:24][O:25][N:26]=[C:27]([C:50]1[N:51]=[CH:52][S:53][CH:54]=1)[C:28]([NH:30][CH:31]1[C:48](=[O:49])[N:33]2[C:34]([C:38]([O:40][CH:41]([O:43][C:44](=[O:47])[CH2:45][CH3:46])[CH3:42])=[O:39])=[CH:35][CH2:36][S:37][C@H:32]12)=[O:29])=[O:23])(C1C=CC=CC=1)C1C=CC=CC=1.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[C:22]([CH2:24][O:25][N:26]=[C:27]([C:50]1[N:51]=[CH:52][S:53][CH:54]=1)[C:28]([NH:30][CH:31]1[C:48](=[O:49])[N:33]2[C:34]([C:38]([O:40][CH:41]([O:43][C:44](=[O:47])[CH2:45][CH3:46])[CH3:42])=[O:39])=[CH:35][CH2:36][S:37][C@H:32]12)=[O:29])([OH:23])=[O:21]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 1317142101-Propionyloxyethyl 7-[2-benzhydryloxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylate

Product 1

HCID 1317142091-Propionyloxyethyl 7-[2-carboxymethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylateYield 51.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (1.4 ml) was added to a suspension of 1-propionyloxyethyl 7-[2-benzhydryloxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylate (syn isomer) (1.2 g) in methylene chloride (10 ml) and anisole (0.8 ml) at ambient temperature and the mixture was stirred for 2 hours at the same temperature. To the resulting solution was added diisopropyl ether (50 ml) and the mixture was stirred. The precipitates were collected by filtration, washed with diisopropyl ether. The precipitates were added to a mixture of ethyl acetate and water, and the mixture was adjusted to pH 7.5 with 20% aqueous solution of potassium carbonate. The separated aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid and extracted with ethyl acetate. The extract layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated. The residue was washed with diisopropyl ether and filtered to give 1-propionyloxyethyl 7-[2-carboxymethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylate (syn isomer) (0.47 g).

Workup

  1. stirringthe mixture was stirred
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with diisopropyl ether
  4. additionThe precipitates were added to a mixture of ethyl acetate and water
  5. extractionextracted with ethyl acetate
  6. washThe extract layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. washThe residue was washed with diisopropyl ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-6580f0fb01df4d5384f3d6317d3c3a13
Source dataset
uspto-grants-1985_05
Patent number
US04515788

Reaction notes

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