Trifluoroacetic acid → HCID 131716067, compound

HRID 1723597Notes

Reaction equation

HRID 1723597 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:47][O:48][CH:49]2[CH2:51][CH2:50]2)[C:8]([NH:10][C@@H:11]2[C:45](=[O:46])[N:13]3[C:14]([C:29]([O:31]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:30])=[C:15]([CH2:18][S:19][C:20]4[N:25]([CH3:26])[C:24](=[O:27])[C:23](=[O:28])[NH:22][N:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C1(OC)C=CC=CC=1.C(Cl)Cl>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:47][O:48][CH:49]2[CH2:51][CH2:50]2)[C:8]([NH:10][C@@H:11]2[C:45](=[O:46])[N:13]3[C:14]([C:29]([OH:31])=[O:30])=[C:15]([CH2:18][S:19][C:20]4[N:25]([CH3:26])[C:24](=[O:27])[C:23](=[O:28])[NH:22][N:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131716051HCID 131716051, compound

Product 1

HCID 131716067HCID 131716067, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a suspension of benzhydryl 7β-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-(5,6-dioxo-4-methyl-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (350 mg) in a mixture of anisol (0.5 ml) and methylene chloride (1.5 ml) was added trifluoroacetic acid (1 ml) under ice-cooling. The mixture was stirred at the same temperature for 30 minutes. The mixture was poured into diisopropyl ether (100 ml) and the resulted precipitate was collected. The precipitate was added to a mixture of ice-water and ethyl acetate and adjusted to pH 7 with saturated aqueous solution of sodium bicarbonate. The aqueous layer was separated and adjusted to pH 3 with 6N hydrochloric acid. The precipitate was collected and dried over phosphorus pentoxide to give 7β-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-(5,6-dioxo-4-methyl-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (157 mg).

Workup

  1. temperaturecooling
  2. customthe resulted precipitate was collected
  3. additionThe precipitate was added to a mixture of ice-water and ethyl acetate
  4. customThe aqueous layer was separated
  5. customThe precipitate was collected
  6. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-6d1e0b435b3c430eb119644daaee443e
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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