2-Benzhydryloxycarbonyl-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene → 7-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-carboxy-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 463582Notes

Reaction equation

HRID 463582 reaction equation
C([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH:25]=[C:26]([S:28][C:29]1[S:33][C:32]([CH3:34])=[N:31][N:30]=1)[CH3:27])[CH:20]([NH:35][C:36](=[O:66])[C:37](=[N:63][O:64][CH3:65])[C:38]1[N:39]=[C:40]([NH:43]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:41][CH:42]=1)[C:19]2=[O:67])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1>C(O)=O>[NH2:43][C:40]1[S:41][CH:42]=[C:38]([C:37](=[N:63][O:64][CH3:65])[C:36]([NH:35][CH:20]2[C:19](=[O:67])[N:18]3[CH:21]2[S:22][CH2:23][C:24]([CH:25]=[C:26]([S:28][C:29]2[S:33][C:32]([CH3:34])=[N:31][N:30]=2)[CH3:27])=[C:17]3[C:15]([OH:16])=[O:14])=[O:66])[N:39]=1

Participants

3

Reactant 1

HCID 536585572-Benzhydryloxycarbonyl-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 537060917-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-carboxy-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-eneYield 13.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

The Z form of the syn isomer of 2-benzhydryloxycarbonyl-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.76 g) is dissolved in formic acid (8 cc). The solution is heated to 50° C. and distilled water (4 cc) is added dropwise in the course of 10 minutes. The mixture is stirred for 30 minutes at 50° C., distilled water (4 cc) is then added, the mixture is cooled and filtered and the solution is concentrated to dryness under reduced pressure (1 mm Hg; 0.13 kPa) at 40° C. Ethanol (40 cc) is added and evaporated off under reduced pressure (1 mm Hg; 0.13 kPa) at 30° C., and this operation is repeated a further 2 times. The residue is taken up in ethanol (10 cc), the solution is filtered, the cake is washed with diethyl ether (20 cc), the filtrate is dried over sodium sulphate and the solvent is evaporated off under reduced pressure (1 mm Hg; 0.13 kPa) at 20° C. The Z form of the syn isomer of 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-carboxy-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (60 mg) is thus isolated in the form of a yellow powder.

Workup

  1. distillationdistilled water (4 cc)
  2. additionis added dropwise in the course of 10 minutes
  3. distillationdistilled water (4 cc)
  4. additionis then added
  5. temperaturethe mixture is cooled
  6. filtrationfiltered
  7. concentrationthe solution is concentrated to dryness under reduced pressure (1 mm Hg; 0.13 kPa) at 40° C
  8. additionEthanol (40 cc) is added
  9. customevaporated off under reduced pressure (1 mm Hg; 0.13 kPa) at 30° C.
  10. filtrationthe solution is filtered
  11. washthe cake is washed with diethyl ether (20 cc)
  12. dry with materialthe filtrate is dried over sodium sulphate
  13. customthe solvent is evaporated off under reduced pressure (1 mm Hg; 0.13 kPa) at 20° C

Sources & evidence

ORD record
ord-0437c4b755e34affaae1f9c972332cf8
Source dataset
uspto-grants-1985_05
Patent number
US04520193

Reaction notes

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