Trifluoroacetic acid → HCID 131714051, compound

HRID 1153948Notes

Reaction equation

HRID 1153948 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:38]1[N:42]=[C:41]([NH2:43])[S:40][N:39]=1)[C:19]([NH:21][CH:22]1[C:36](=[O:37])[N:24]2[C:25]([C:33]([OH:35])=[O:34])=[C:26]([CH2:29][N:30]=[N+:31]=[N-:32])[CH2:27][S:28][C@H:23]12)=[O:20])=[O:14])(C)(C)C.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[C:13]([CH2:15][O:16][N:17]=[C:18]([C:38]1[N:42]=[C:41]([NH2:43])[S:40][N:39]=1)[C:19]([NH:21][CH:22]1[C:36](=[O:37])[N:24]2[C:25]([C:33]([OH:35])=[O:34])=[C:26]([CH2:29][N:30]=[N+:31]=[N-:32])[CH2:27][S:28][C@H:23]12)=[O:20])([OH:14])=[O:12]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131714052HCID 131714052, compound

Product 1

HCID 131714051HCID 131714051, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (18 ml) was added to a suspension of 7-[2-t-butoxycarbonylmethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-azidomethyl-3-cephem-4-carboxylic acid (syn isomer) (4.6 g) in methylene chloride (10 ml) and anisole (5 ml), and the mixture was stirred for 7 hours at ambient temperature. The reaction mixture was added dropwise to diisopropyl ether (200 ml) and precipitates were collected by filtration. The precipitates were added to a mixture of water and ethyl acetate, and the mixture was adjusted to pH 7.0 with saturated aqueous solution of sodium bicarbonate. The separated aqueous layer was adjusted to pH 3.0 with 10% hydrochloric acid. The precipitates were collected by filtration and successively washed with water to give 7-[2-carboxymethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-azidomethyl-3-cephem-4-carboxylic acid (syn isomer). (2.7 g).

Workup

  1. customprecipitates
  2. filtrationwere collected by filtration
  3. additionThe precipitates were added to a mixture of water and ethyl acetate
  4. filtrationThe precipitates were collected by filtration
  5. washsuccessively washed with water

Sources & evidence

ORD record
ord-e40eff3fc2e44872925c1c9b47d82fe5
Source dataset
uspto-grants-1984_12
Patent number
US04487768

Reaction notes

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