Boron trifluoride etherate → HCID 131715001, compound

HRID 1249423Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:39][OH:40])[C:8]([NH:10][CH:11]2[C:37](=[O:38])[N:13]3[C:14]([C:21]([O:23]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:22])=[C:15](/[CH:18]=[CH:19]/[Cl:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.B(F)(F)F.CCOCC>C(O)(=O)C.C1(OC)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>[OH:40][N:39]=[C:7]([C:5]1[N:6]=[C:2]([NH2:1])[S:3][CH:4]=1)[C:8]([NH:10][CH:11]1[C:37](=[O:38])[N:13]2[C:14]([C:21]([OH:23])=[O:22])=[C:15](/[CH:18]=[CH:19]/[Cl:20])[CH2:16][S:17][C@H:12]12)=[O:9]

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (syn isomer) (2.5 g) in a mixture of acetic acid (2.5 ml) and anisole (9.6 ml) was dropwise added boron trifluoride etherate (2.5 ml) at 3° C. and the mixture was stirred for 30 minutes at the same temperature for 30 minutes. The reaction mixture was dissolved in 20% aqueous solution of potassium carbonate, washed with ethyl acetate, concentrated to remove the organic solvent under reduced pressure, cooled to 5° C. and adjusted to pH 2.3 with 10% hydrochloric acid. The resultant precipitates were collected by filtration, washed with water and dried in vacuo to give 7-[2-hydroxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylic acid (syn isomer) (2.65 g)

Workup

customat 3° C.
washwashed with ethyl acetate
concentrationconcentrated
customto remove the organic solvent under reduced pressure
customThe resultant precipitates
filtrationwere collected by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-22e9a4d0cd6a461ca4a8822534add929
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04631274

Reaction notes

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