Trifluoroacetic acid → HCID 70266526, compound

HRID 1858522Notes

Reaction equation

HRID 1858522 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:61](=[O:62])[N:13]3[C:14]([C:45]([O:47]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:46])=[C:15]([S:18][CH2:19][CH2:20][C:21]4[CH:22]=[N:23][N:24](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:25]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl.C1(OC)C=CC=CC=1>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:61](=[O:62])[N:13]3[C:14]([C:45]([OH:47])=[O:46])=[C:15]([S:18][CH2:19][CH2:20][C:21]4[CH:22]=[N:23][NH:24][CH:25]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 70265603HCID 70265603, compound

Product 1

HCID 70266526HCID 70266526, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of benzhydryl 7β-(2-phenylacetamido)-3-[2-(1-tritylpyrazol-4-yl)ethylthio]-3-cephem-4-carboxylate (930 mg) in a mixture of dichloromethane (3 ml) and anisole (1 ml) was added trifluoroacetic acid (2 ml) under ice-cooling. The mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into diisopropyl ether (100 ml). The precipitate was collected by filtration. The precipitate was added a 90% formic acid (4 ml) and stirred for 15 minutes at room temperature. The reaction mixture was poured into a mixture of ethyl acetate (100 ml) and ice-water (50 ml). The separated organic layer was added buffer solution (pH 6.86, 100 ml), adjusted to pH 7 with sodium bicarbonate. The separated aqueous layer was added ethyl acetate (60 ml) and tetrahydrofuran (30 ml), adjusted to pH 2.5 with 1N-hydrochloric acid. The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether to give 7β-(2-phenylacetamido)-3-[2-(pyrazol-4-yl)ethylthio]-3-cephem-4-carboxylic acid (275 mg).

Workup

  1. temperaturecooling
  2. filtrationThe precipitate was collected by filtration
  3. additionThe precipitate was added a 90% formic acid (4 ml)
  4. stirringstirred for 15 minutes at room temperature
  5. additionThe reaction mixture was poured into a mixture of ethyl acetate (100 ml) and ice-water (50 ml)
  6. additionThe separated organic layer was added buffer solution (pH 6.86, 100 ml)
  7. additionThe separated aqueous layer was added ethyl acetate (60 ml) and tetrahydrofuran (30 ml)
  8. washThe organic layer was washed with saturated aqueous sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-40ef446d7c4a4bf99d03f12ea802a917
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

Loading…