Trifluoroacetic acid → HCID 131714768, compound

HRID 1650925Notes

Reaction equation

HRID 1650925 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:10][C:11]([Cl:47])=[C:12]([C:14](=[N:37][O:38][CH2:39][C:40]([O:42]C(C)(C)C)=[O:41])[C:15]([NH:17][CH:18]2[C:35](=[O:36])[N:20]3[C:21]([C:32]([OH:34])=[O:33])=[C:22]([CH2:25][S:26][C:27]4[S:28][CH:29]=[N:30][N:31]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[NH2:8][C:9]1[S:10][C:11]([Cl:47])=[C:12]([C:14](=[N:37][O:38][CH2:39][C:40]([OH:42])=[O:41])[C:15]([NH:17][CH:18]2[C:35](=[O:36])[N:20]3[C:21]([C:32]([OH:34])=[O:33])=[C:22]([CH2:25][S:26][C:27]4[S:28][CH:29]=[N:30][N:31]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131714767HCID 131714767, compound

Product 1

HCID 131714768HCID 131714768, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (10 ml) was added to a solution of 7-[2-(2-amino-5-chlorothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.5 g) in methylene chloride (5.0 ml) and anisole (2.5 ml) under ice-cooling, and then the mixture was stirred for an hour at ambient temperature. The resulting solution was dropwise added to diisopropyl ether (100 ml) and then precipitates were collected by filtration. The precipitates were added to a mixture of water and ethyl acetate, and adjusted to pH 7.5 with 10% aqueous solution of sodium hydroxide. The aqueous layer was separated and adjusted to pH 2.2 with 10% aqueous hydrochloric acid to give the precipitates, which were filtered off and dried over phosphorus pentoxide in vacuo to give 7-[2-(2-amino-5-chlorothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(1.83 g).

Workup

  1. temperaturecooling
  2. customprecipitates
  3. filtrationwere collected by filtration
  4. additionThe precipitates were added to a mixture of water and ethyl acetate
  5. customThe aqueous layer was separated
  6. customto give the precipitates, which
  7. filtrationwere filtered off
  8. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-562b144d74fa48c5a2456db4653d4957
Source dataset
uspto-grants-1990_05
Patent number
US04925948

Reaction notes

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