Trifluoroacetic acid → HCID 131712592, compound

HRID 1659755Notes

Reaction equation

HRID 1659755 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:44]1[N:45]=[C:46]([NH2:49])[S:47][CH:48]=1)[C:19]([NH:21][CH:22]1[C:42](=[O:43])[N:24]2[C:25]([C:39]([OH:41])=[O:40])=[C:26]([CH2:29][S:30][C:31]3[N:35]([CH2:36][CH:37]=[CH2:38])[N:34]=[N:33][N:32]=3)[CH2:27][S:28][C@H:23]12)=[O:20])=[O:14])(C)(C)C>C1(OC)C=CC=CC=1>[C:13]([CH2:15][O:16][N:17]=[C:18]([C:44]1[N:45]=[C:46]([NH2:49])[S:47][CH:48]=1)[C:19]([NH:21][CH:22]1[C:42](=[O:43])[N:24]2[C:25]([C:39]([OH:41])=[O:40])=[C:26]([CH2:29][S:30][C:31]3[N:35]([CH2:36][CH:37]=[CH2:38])[N:34]=[N:33][N:32]=3)[CH2:27][S:28][C@H:23]12)=[O:20])([OH:14])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131712593HCID 131712593, compound

Product 1

HCID 131712592HCID 131712592, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (20 ml) was added under ice-cooling to a stirred suspension of 7-[2-t-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(2.05 g) in anisole (2 ml), and the resultant mixture was stirred for 2 hours at ambient temperature. The reaction mixture was concentrated under reduced pressure and diethyl ether was added thereto. Precipitates were collected by filtration, washed with diethyl ether, dried and dissolved in an aqueous solution of sodium bicarbonate. An insoluble material was filtered off and the filtrate was adjusted to pH 3.2 with conc.hydrochloride acid. Precipitates were collected by filtration, washed with water and dried to give 7-[2-carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.8 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and diethyl ether
  2. additionwas added
  3. customPrecipitates
  4. filtrationwere collected by filtration
  5. washwashed with diethyl ether
  6. customdried
  7. dissolutiondissolved in an aqueous solution of sodium bicarbonate
  8. filtrationAn insoluble material was filtered off
  9. customPrecipitates
  10. filtrationwere collected by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-8a2541a44f024ef5823ed89c26c83a68
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

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