Trifluoroacetic acid → HCID 131714211, compound

HRID 648844Notes

Reaction equation

HRID 648844 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:49]1[N:50]=[CH:51][S:52][CH:53]=1)[C:19]([NH:21][CH:22]1[C:47](=[O:48])[N:24]2[C:25]([C:31]([O:33]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:32])=[C:26]([CH:29]=[CH2:30])[CH2:27][S:28][C@H:23]12)=[O:20])=[O:14])(C)(C)C.C(OC(C)C)(C)C.CCCCCC>C(Cl)Cl.C1(OC)C=CC=CC=1>[C:13]([CH2:15][O:16][N:17]=[C:18]([C:49]1[N:50]=[CH:51][S:52][CH:53]=1)[C:19]([NH:21][CH:22]1[C:47](=[O:48])[N:24]2[C:25]([C:31]([OH:33])=[O:32])=[C:26]([CH:29]=[CH2:30])[CH2:27][S:28][C@H:23]12)=[O:20])([OH:14])=[O:12]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 8058HexaneHCID 131714212HCID 131714212, compound

Product 1

HCID 131714211HCID 131714211, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (11.2 ml) was added to a stirred suspension of benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (2.8 g) in methylene chloride (5.6 ml) and anisole (2.8 ml) at ambient temperature and the mixture was stirred for 1.5 hours at the same temperature. To the resultant solution was added diisopropyl ether (40 ml) and n-hexane (30 ml) and the mixture was stirred. The precipitates were collected by filtration, washed with a solution of diisopropyl ether and n-hexane (1:1). The precipitates were added to a mixture of ethyl acetate and water and the mixture was adjusted to pH 7.0 with a saturated aqueous solution of potassium carbonate. The separated aqueous layer was adjusted to pH 4.0 with 10% hydrochloric acid and the solution was washed with ethyl acetate. The aqueous layer was adjusted to pH 1.8 with 10% hydrochloric acid and saturated with sodium chloride. The acidic solution was extracted with ethyl acetate and tetrahydrofuran (1:1). The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 7-[2-carboxymethoxyimino-2-(4-thiazolyl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (1.22 g).

Workup

  1. stirringthe mixture was stirred
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with a solution of diisopropyl ether and n-hexane (1:1)
  4. additionThe precipitates were added to a mixture of ethyl acetate and water
  5. washthe solution was washed with ethyl acetate
  6. extractionThe acidic solution was extracted with ethyl acetate and tetrahydrofuran (1:1)
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-727f9112eac54fdf849ca7b48727b40c
Source dataset
uspto-grants-1988_04
Patent number
US04736039

Reaction notes

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