Hydrochloric Acid → HCID 54206503, compound

HRID 1164685Notes

Reaction equation

HRID 1164685 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([O:22][CH2:23][C:24]=1[CH:25]=[CH:26]N(C)C)[CH:20]([NH:30][C:31](=[O:61])[C:32](=[N:58][O:59][CH3:60])[C:33]1[N:34]=[C:35]([NH:38][C:39]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[S:36][CH:37]=1)[C:19]2=[O:62])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(OCC)(=[O:66])C>>[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([O:22][CH2:23][C:24]=1[CH2:25][CH:26]=[O:66])[CH:20]([NH:30][C:31](=[O:61])[C:32](=[N:58][O:59][CH3:60])[C:33]1[N:34]=[C:35]([NH:38][C:39]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[S:36][CH:37]=1)[C:19]2=[O:62])=[O:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 54139800HCID 54139800, compound

Product 1

HCID 54206503HCID 54206503, compound

Procedure

A solution of the E form of the syn isomer of 2-benzhydryloxycarbonyl-3-(2-dimethylaminovinyl)-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene (1.05 g) in ethyl acetate (10 cc) is stirred vigorously for 1 hour at 20° C., in the presence of a 1 N solution of hydrochloric acid (5 cc). The mixture is separated by decantation and the organic phase is washed with a saturated solution of sodium bicarbonate (10 cc), distilled water (10 cc) and a saturated solution of sodium chloride (10 cc). The ethyl acetate phase is dried over anhydrous magnesium sulphate and filtered and the filtrate is concentrated to dryness at 30° C. under reduced pressure (20 mm Hg; 2.7 kPa). This yields the syn isomer of 2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-3-(2-oxoethyl)-5-oxa-1-azabicyclo[4.2.0]-oct-2-ene (1.00 g) in the form of a hard yellow foam.

Workup

  1. customThe mixture is separated by decantation
  2. washthe organic phase is washed with a saturated solution of sodium bicarbonate (10 cc)
  3. distillationdistilled water (10 cc)
  4. dry with materialThe ethyl acetate phase is dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness at 30° C. under reduced pressure (20 mm Hg; 2.7 kPa)

Sources & evidence

ORD record
ord-fd3c35e8678a48d5873eed8a241b6e0b
Source dataset
uspto-grants-1983_01
Patent number
US04370478

Reaction notes

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