HCID 54403034, compound → HCID 53939500, compound

HRID 1660314Notes

Reaction equation

HRID 1660314 reaction equation
C([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH:25]=[CH:26][O:27][S:28]([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH:20]([NH:38][C:39](=[O:69])[C:40](=[N:66][O:67][CH3:68])[C:41]1[N:42]=[C:43]([NH:46]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:44][CH:45]=1)[C:19]2=[O:70])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1>C(O)=O>[NH2:46][C:43]1[S:44][CH:45]=[C:41]([C:40](=[N:66][O:67][CH3:68])[C:39]([NH:38][CH:20]2[C:19](=[O:70])[N:18]3[CH:21]2[S:22][CH2:23][C:24]([CH:25]=[CH:26][O:27][S:28]([C:31]2[CH:32]=[CH:33][C:34]([CH3:35])=[CH:36][CH:37]=2)(=[O:29])=[O:30])=[C:17]3[C:15]([OH:16])=[O:14])=[O:69])[N:42]=1

Participants

3

Reactant 1

HCID 54403034HCID 54403034, compound

Product 1

HCID 53939500HCID 53939500, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

2-Benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylamino-thiazol-4-yl)-acetamido]-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (syn isomer, E-form) (1.5 g) is dissolved in a mixture of formic acid (30 cc) and distilled water (10 cc). The solution is heated at 50° C. for 30 minutes. After it has cooled, the precipitate is filtered off and the filtrate is concentrated to dryness under reduced pressure (10 mm Hg) at 30° C. The residue is triturated with diethyl ether (50 cc). The solidified product is filtered off, washed with diethyl ether (two×25 cc) and then dried under reduced pressure (5 mm Hg) at 25° C. 7-[2-(2-Amino-thiazol-4-yl)-2-methoxyimino-acetamido]-2-carboxy-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (syn isomer, E-form) (0.75 g) is obtained as a solvate with formic acid.

Workup

  1. distillationdistilled water (10 cc)
  2. temperatureAfter it has cooled
  3. filtrationthe precipitate is filtered off
  4. concentrationthe filtrate is concentrated to dryness under reduced pressure (10 mm Hg) at 30° C
  5. customThe residue is triturated with diethyl ether (50 cc)
  6. filtrationThe solidified product is filtered off
  7. washwashed with diethyl ether (two×25 cc)
  8. customdried under reduced pressure (5 mm Hg) at 25° C

Sources & evidence

ORD record
ord-56ca0cf37ad3453ba29828570b402e93
Source dataset
uspto-grants-1981_12
Patent number
US04307116

Reaction notes

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