Trifluoroacetic acid → HCID 131713154, compound

HRID 1494494Notes

Reaction equation

HRID 1494494 reaction equation
C([O:14][C:15]([CH2:17][O:18][N:19]=[C:20]([C:52]1[N:53]=[C:54]([NH:57][C:58](=[O:63])[C:59]([F:62])([F:61])[F:60])[S:55][CH:56]=1)[C:21]([NH:23][CH:24]1[C:50](=[O:51])[N:26]2[C:27]([C:34]([O:36]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:35])=[C:28]([CH2:31][S:32][CH3:33])[CH2:29][S:30][C@H:25]12)=[O:22])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C(Cl)Cl>[C:15]([CH2:17][O:18][N:19]=[C:20]([C:52]1[N:53]=[C:54]([NH:57][C:58](=[O:63])[C:59]([F:60])([F:62])[F:61])[S:55][CH:56]=1)[C:21]([NH:23][CH:24]1[C:50](=[O:51])[N:26]2[C:27]([C:34]([OH:36])=[O:35])=[C:28]([CH2:31][S:32][CH3:33])[CH2:29][S:30][C@H:25]12)=[O:22])([OH:16])=[O:14]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131713155Benzhydryl 7-[2-benzhydryloxycarbonylmethoxyimino-2-{2-(2,2,2-trifluoroacetamido)-thiazol-4-yl}acetamido]-3-methylthiomethyl-3-cephem-4-carboxylate

Product 1

HCID 131713154HCID 131713154, compoundYield 117.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 7-[2-benzhydryloxycarbonylmethoxyimino-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-methylthiomethyl-3-cephem-4-carboxylate (syn isomer)(5.6 g) and anisole(5.6 ml) in methylene chloride (11.2 ml) was added trifluoroacetic acid (11.2 ml) at 10° C. The mixture was stirred for 1.5 hours at ambient temperature and then poured into a mixture of diisopropyl ether (400 ml) and petroleum ether (100 ml). The precipitates were collected by filtration and washed with petroleum ether to give 7-[2-carboxymethoxyimino-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-methylthiomethyl-3-cephem-4-carboxylic acid (syn isomer) (4.2 g), mp 183°-186° C. (dec.).

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with petroleum ether

Sources & evidence

ORD record
ord-6963ad2b89c64b4189f41466309b843b
Source dataset
uspto-grants-1991_06
Patent number
US05026695

Reaction notes

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