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

HRID 1906083Notes

Reaction equation

HRID 1906083 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 mxture 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 soluiton 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 mxture 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 soluiton 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-2842ea0a9a0f4043ad93a2a90d56e419
Source dataset
uspto-grants-1987_03
Patent number
US04649136

Reaction notes

Loading…