Trifluoroacetic acid → (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-but-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 247754Notes

Reaction equation

HRID 247754 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:40]/[O:41][CH3:42])/[C:8]([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:22]([O:24]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:23])=[C:15](/[CH:18]=[CH:19]\[CH2:20][CH3:21])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:40]/[O:41][CH3:42])/[C:8]([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:22]([OH:24])=[O:23])=[C:15](/[CH:18]=[CH:19]\[CH2:20][CH3:21])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 88669278benzhydryl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-but-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 88669631(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-but-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 52.2%

Procedure

A mixture of diphenylmethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-1-butenyl]-3-cephem-4-carboxylate (1.65 g, 2.65 mmoles) and anisole (0.5 ml) was treated with TFA (5 ml) at room temperature for 1 hour. The mixture was diluted with IPE. The resulting precipitate*1 was collected by filtration and chromatographed on a column of the packing (50 ml) of a PrepPAK cartridge (Waters) with 20-30% methanol to yield 605 mg (52%) of the title compound. Estimated purity 90% (by HPLC). Mp.>160° C. (grad. dec.).

Workup

  1. additionThe mixture was diluted with IPE
  2. filtrationThe resulting precipitate*1 was collected by filtration
  3. customchromatographed on a column of the packing (50 ml) of a PrepPAK cartridge (Waters) with 20-30% methanol

Sources & evidence

ORD record
ord-aed715da6bb34e429390d18e5d360f61
Source dataset
uspto-grants-1987_11
Patent number
US04708955

Reaction notes

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