Trifluoroacetic acid → sodium 7beta-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate

HRID 1074359Notes

Reaction equation

HRID 1074359 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:46][O:47][CH:48]2[CH2:50][CH2:49]2)[C:8]([NH:10][C@@H:11]2[C:44](=[O:45])[N:13]3[C:14]([C:28]([O:30]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:29])=[C:15]([CH2:18][S:19]/[CH:20]=[CH:21]\[C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C.C(=O)(O)[O-].[Na+:77]>C(Cl)Cl.C(OCC)(=O)C.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:46][O:47][CH:48]2[CH2:50][CH2:49]2)[C:8]([NH:10][C@@H:11]2[C:44](=[O:45])[N:13]3[C:14]([C:28]([O-:30])=[O:29])=[C:15]([CH2:18][S:19]/[CH:20]=[CH:21]\[C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+:77]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 516892Sodium BicarbonateHCID 131716063benzhydryl 7beta-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate

Product 1

HCID 131716723sodium 7beta-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzhydryl 7β-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (0.69 g), anisole (0.69 ml), and trifluoroacetic acid (2.07 ml) in methylene chloride (1.38 ml) was stirred under ice-cooling for 40 minutes. The mixture was poured into diisopropyl ether to give a precipitate. The precipitate was dissolved into a mixture of water (30 ml) and ethyl acetate (15 ml) and the solution was adjusted to pH 7.1 with saturated aqueous solution of sodium bicarbonate. The aqueous layer was separated and adjusted to pH 5.6 with 1N hydrochloric acid. The solution was subjected to column chromatography on a non-ionic adsorption resin "Diaion HP-20" (12 ml). After the column was washed with water, the elution was carried out with 20% isopropyl alcohol. The fractions containing the object compound were combined, concentrated in vacuo to about 20 ml and lyophylized to give sodium 7β-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (0.30 g).

Workup

  1. temperaturecooling for 40 minutes
  2. customto give a precipitate
  3. customThe aqueous layer was separated
  4. washAfter the column was washed with water
  5. washthe elution
  6. additionThe fractions containing the object compound
  7. concentrationconcentrated in vacuo to about 20 ml

Sources & evidence

ORD record
ord-4f81bd3149734f8789b77830be270619
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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