HCID 54234928, compound → HCID 54381801, compound

HRID 463594Notes

Reaction equation

HRID 463594 reaction equation
C([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27])[CH:20]([NH:34][C:35](=[O:65])[C:36](=[N:62][O:63][CH3:64])[C:37]1[N:38]=[C:39]([NH:42]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:40][CH:41]=1)[C:19]2=[O:66])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1>C(O)=O.O>[NH2:42][C:39]1[S:40][CH:41]=[C:37]([C:36](=[N:62][O:63][CH3:64])[C:35]([NH:34][CH:20]2[C:19](=[O:66])[N:18]3[CH:21]2[S:22][CH2:23][C:24]([CH2:25][C:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:27])=[C:17]3[C:15]([OH:16])=[O:14])=[O:65])[N:38]=1

Participants

4

Reactant 1

HCID 54234928HCID 54234928, compound

Product 1

HCID 54381801HCID 54381801, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
45 °C

Procedure

The syn isomer of 2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4yl)-acetamido]-8-oxo-3-phenacyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene (2.7 g) is dissolved in formic acid (55 cc) at 20° C. Distilled water (11 cc) is added and the mixture is heated for 15 minutes at 45° C. The mixture is cooled to 20° C., diluted with water (44 cc) and filtered. The filtrate is concentrated to dryness under reduced pressure (5 mm Hg; 0.67 kPa) at 20° C. The residue is taken up in ethanol (3×50 cc), the solvent being evaporated off each time under reduced pressure (5 mm Hg; 0.67 kPa) at 20° C. in order to remove the water and the formic acid. The final residue is taken up in a saturated solution of sodium bicarbonate (50 cc) and the aqueous phase is washed with ethyl acetate (50 cc) and acidified to pH 3 with 1N hydrochloric acid, whilst stirring, in the presence of ethyl acetate (100 cc). The organic phase is dried over magnesium sulphate and evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. This yields the syn isomer of 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-carboxy-8-oxo-3-phenacyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.54 g) in the form of a beige solid.

Workup

  1. temperatureThe mixture is cooled to 20° C.
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated to dryness under reduced pressure (5 mm Hg; 0.67 kPa) at 20° C
  4. customthe solvent being evaporated off each time under reduced pressure (5 mm Hg; 0.67 kPa) at 20° C. in order
  5. customto remove the water
  6. washthe aqueous phase is washed with ethyl acetate (50 cc)
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. customevaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C

Sources & evidence

ORD record
ord-dff62cfaf3ab4051b092f77720dfbd47
Source dataset
uspto-grants-1985_05
Patent number
US04520193

Reaction notes

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