Boron trifluoride etherate → HCID 131714458, compound

HRID 638088Notes

Reaction equation

HRID 638088 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:38][OH:39])[C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.B(F)(F)F.CCOCC.O1CCCC1.[OH-].[Na+]>C1(OC)C=CC=CC=1.C(O)(=O)C.O.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:38][OH:39])[C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

9

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 131714454HCID 131714454, compound

Product 1

HCID 131714458HCID 131714458, compoundYield 34.9%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 7519AnisoleSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (5 g) in a mixture of anisole (20 ml) and acetic acid (5 ml) was added dropwise boron trifluoride etherate (5 ml) at 10° C. After stirring for 20 minutes at 10° C., the reaction mixture was poured into a mixture of tetrahydrofuran (100 ml), ethyl acetate (100 ml) and water (100 ml), and then adjusted to pH 6.0 with 20% aqueous sodium hydroxide. The resultant aqueous layer was separated and washed with ethyl acetate under keeping the pH value at 6.0. This solution was subjected to chromatography on aluminum oxide. The fractions eluted with 3% aqueous sodium acetate were collected and adjusted to pH 4.0 with 10% hydrochloric acid. This solution was further chromatographed on nonionic adsorption resin "Diaion HP-20" (Trademark, manufactured by Mitsubishi Chemical Industries). The fractions eluted with 20% aqueous acetone were collected, concentrated in vacuo and adjusted to pH 2.0 with 10% hydrochloric acid. The resultant precipitate was collected by filtration and dried in vacuo to give 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (1.23 g).

Workup

  1. customThe resultant aqueous layer was separated
  2. washwashed with ethyl acetate
  3. washThe fractions eluted with 3% aqueous sodium acetate
  4. customwere collected
  5. customThis solution was further chromatographed on nonionic adsorption resin "Diaion
  6. washThe fractions eluted with 20% aqueous acetone
  7. customwere collected
  8. concentrationconcentrated in vacuo
  9. filtrationThe resultant precipitate was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-b70eab2cc45d4c94b45325475d264205
Source dataset
uspto-grants-1985_12
Patent number
US04559334

Reaction notes

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