Hydrochloric Acid → HCID 20514849, compound

HRID 1902804Notes

Reaction equation

HRID 1902804 reaction equation
C([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1C=CN(C)C)[CH:20]([NH:30][C:31]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:19]2=[O:50])=O)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.[C:52]([O:55][CH2:56][CH3:57])(=[O:54])[CH3:53]>>[CH:56]([O:55][C:52]([C:53]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH2:17][CH:15]=[O:14])[CH:20]([NH:30][C:31]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:19]2=[O:50])=[O:54])([C:37]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:57]1[CH:39]=[CH:38][CH:31]=[CH:44][CH:45]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 53847685HCID 53847685, compound

Product 1

HCID 20514849HCID 20514849, compound

Procedure

A solution of 2-benzhydryloxycarbonyl-3-(2-dimethylaminovinyl)-8-oxo-7-tritylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (E-form) (23.5 g) in ethyl acetate (500 cc) is stirred with 1 N hydrochloric acid (250 cc) for 90 minutes at 25° C. The organic phase is decanted, washed with distilled water (3×250 cc), a saturated sodium bicarbonate solution (100 cc) and a half-saturated sodium chloride solution (250 cc), then dried over sodium sulphate and concentrated to dryness under reduced pressure (40 mm Hg) at 40° C. 2-Benzhydryloxycarbonyl-8-oxo-3-(2-oxo-ethyl)-7-tritylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (21 g) is obtained in the form of an orange-coloured froth.

Workup

  1. customThe organic phase is decanted
  2. washwashed with distilled water (3×250 cc)
  3. dry with materiala saturated sodium bicarbonate solution (100 cc) and a half-saturated sodium chloride solution (250 cc), then dried over sodium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (40 mm Hg) at 40° C

Sources & evidence

ORD record
ord-5d5375cbd2b14e49a898cf85a1acc94f
Source dataset
uspto-grants-1982_12
Patent number
US04365062

Reaction notes

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