(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acid → HCID 53839652, compound

HRID 1660378Notes

Reaction equation

HRID 1660378 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH3:32])[C:27]([OH:29])=O)[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([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.[NH2:33][CH:34]1[C:41](=[O:42])[N:40]2[CH:35]1[S:36][CH2:37][C:38]([CH3:59])=[C:39]2[C:43]([O:45][CH:46]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44]>C(Cl)Cl>[CH:46]([O:45][C:43]([C:39]1[N:40]2[CH:35]([S:36][CH2:37][C:38]=1[CH3:59])[CH:34]([NH:33][C:27](=[O:29])[C:26](=[N:30][O:31][CH3:32])[C:24]1[N:25]=[C:21]([NH:20][C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:22][CH:23]=1)[C:41]2=[O:42])=[O:44])([C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

4

Reactant 2

HCID 2724510(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acidHCID 11428945HCID 11428945, compound

Product 1

HCID 53839652HCID 53839652, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2-tritylamino-thiazol-4-yl)-2-methoxyimino-acetic acid (syn isomer) (7.2 g) in methylene chloride (22.4 cc) is added, in a single shot, to a solution of 7-amino-2-benzhydryloxycarbonyl-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (3.15 g) in methylene chloride (31.5 cc). The temperature rises from 8° to 14° C. The mixture is kept stirred for one hour 15 minutes, during which the temperature rises to 20° C., and is then washed with 0.5 N hydrochloric acid (10 cc), distilled water (10 cc) and a saturated sodium bicarbonate solution (20 cc). The insoluble matter formed is filtered off, and the organic phase is washed again with distilled water (2×20 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 mm Hg) at 40° C. The residue is chromatographed on a column (diameter: 3 cm, height: 33 cm) containing silica gel (125 g), elution being carried out with a 20:80 (by volume) mixture of ethyl acetate and cyclohexane (1.2 liters) and then with a 40:60 (by volume) mixture (1 liter), and 50 cc fractions of eluate being collected. Fractions 31 to 44 are evaporated and 2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylamino-thiazol-4yl)-acetamido]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene, syn isomer (2.8 g) is obtained in the form of a pale yellow solid.

Workup

  1. customrises from 8° to 14° C
  2. customrises to 20° C.
  3. washis then washed with 0.5 N hydrochloric acid (10 cc)
  4. distillationdistilled water (10 cc)
  5. customThe insoluble matter formed
  6. filtrationis filtered off
  7. washthe organic phase is washed again with distilled water (2×20 cc)
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure (20 mm Hg) at 40° C
  11. customThe residue is chromatographed on a column (diameter: 3 cm, height: 33 cm)
  12. additioncontaining
  13. washsilica gel (125 g), elution
  14. additionbeing carried out with a 20:80 (by volume) mixture of ethyl acetate and cyclohexane (1.2 liters)
  15. customwith a 40:60 (by volume) mixture (1 liter), and 50 cc fractions of eluate being collected
  16. customFractions 31 to 44 are evaporated

Sources & evidence

ORD record
ord-37304f364b63488eba8672589f80f8c9
Source dataset
uspto-grants-1981_12
Patent number
US04307233

Reaction notes

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