Trifluoroacetic acid → 7beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid

HRID 1609667Notes

Reaction equation

HRID 1609667 reaction equation
FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.[NH2:16][C:17]1[S:21][N:20]=[C:19]([C:22](=[N:53][O:54][CH2:55][C:56]([OH:58])=[O:57])[C:23]([NH:25][C@@H:26]2[C:51](=[O:52])[N:28]3[C:29]([C:35]([O:37]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:36])=[C:30]([CH2:33][Cl:34])[CH2:31][S:32][C@H:27]23)=[O:24])[N:18]=1.C(OC(C)C)(C)C>C(Cl)Cl.CCCCCC>[NH2:16][C:17]1[S:21][N:20]=[C:19]([C:22](=[N:53][O:54][CH2:55][C:56]([OH:58])=[O:57])[C:23]([NH:25][C@@H:26]2[C:51](=[O:52])[N:28]3[C:29]([C:35]([OH:37])=[O:36])=[C:30]([CH2:33][Cl:34])[CH2:31][S:32][C@H:27]23)=[O:24])[N:18]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131718944Benzhydryl 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

Product 1

HCID 1317189457beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acidYield 106%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of trifluoroacetic acid (20 ml) and anisole (10 ml) in methylene chloride (50 ml) was added benzhydryl 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl) -2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (7.0 g) at 0°~5° C. under stirring. The stirring was continued for 2 hours at the same temperature. The reaction mixture was poured into a cold mixture of diisopropyl ether (400 ml) and n-hexane (200 ml). The resulting precipitates were collected by filtration to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid (syn isomer) (5.5 g).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-4884ab657e2a474eb78b7a955b4026e9
Source dataset
uspto-grants-1995_03
Patent number
US05401734

Reaction notes

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