Sodium Chloride → HCID 54136343, compound

HRID 1902789Notes

Reaction equation

HRID 1902789 reaction equation
[CH3:1][N:2]([CH:4](N(C)C)OC(C)(C)C)[CH3:3].[CH:13]([O:26][C:27]([C:29]1[N:30]2[CH:33]([S:34][CH2:35][C:36]=1[CH3:37])[CH:32]([NH:38][C:39](=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:31]2=[O:47])=[O:28])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Na+]>CN(C)C=O.C(OCC)(=O)C.C1CCCCC1>[CH:13]([O:26][C:27]([C:29]1[N:30]2[CH:33]([S:34][CH2:35][C:36]=1[CH:37]=[CH:1][N:2]([CH3:4])[CH3:3])[CH:32]([NH:38][C:39](=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:31]2=[O:47])=[O:28])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 20514829HCID 20514829, compound

Product 1

HCID 54136343HCID 54136343, compoundYield 38.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
25 °C

Procedure

bis-Dimethylamino-tert.-butoxymethane (10 g) is added, under a dry nitrogen atmosphere, to a solution of 2-benzhydryloxycarbonyl-7-benzoylamino-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (24 g) in anhydrous N,N-dimethylformamide (100 cc). The reaction mixture is stirred at 25° C. for 23 hours and is then poured into a mixture of ethyl acetate (300 cc) and an aqueous saturated sodium chloride solution (700 cc). The aqueous phase is decanted and extracted with ethyl acetate (250 cc). The organic phases are combined, washed with 1 N aqueous hydrochloric acid (250 cc), with distilled water (500 cc) and with a saturated aqueous sodium chloride solution (300 cc) and then dried over magnesium sulphate in the presence of decolorising charcoal, and filtered. The solvent is evaporated under reduced pressure (20 mm Hg) at 30° C. The residue is dissolved in methylene chloride (200 cc) and fixed to silica (50 g). The powder obtained is placed in a column (height 60 cm, diameter 5 cm) containing silica gel (415 g) in a 95:5 (by volume) mixture of cyclohexane and ethyl acetate. Elution is carried out with the following mixtures of cyclohexane and ethyl acetate: 95:5 (by volume) (5 liters), 90:10 (by volume) (5 liters), 80:20 (by volume) (5 liters), 70:30 (by volume) (7.5 liters) (so as to elute the impurities) and 60:40 (by volume) (8 liters) the latter being collected and concentrated to dryness. 2-Benzhydryloxycarbonyl-7-benzoylamino-3-(2-dimethylamino-vinyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2 -ene (E-form) (10.4 g) is obtained in the form of a yellow solid.

Workup

  1. customThe aqueous phase is decanted
  2. extractionextracted with ethyl acetate (250 cc)
  3. washwashed with 1 N aqueous hydrochloric acid (250 cc), with distilled water (500 cc) and with a saturated aqueous sodium chloride solution (300 cc)
  4. dry with materialdried over magnesium sulphate in the presence of decolorising charcoal
  5. filtrationfiltered
  6. customThe solvent is evaporated under reduced pressure (20 mm Hg) at 30° C
  7. dissolutionThe residue is dissolved in methylene chloride (200 cc)
  8. customThe powder obtained
  9. additioncontaining silica gel (415 g)
  10. washElution
  11. wash95:5 (by volume) (5 liters), 90:10 (by volume) (5 liters), 80:20 (by volume) (5 liters), 70:30 (by volume) (7.5 liters) (so as to elute the impurities) and 60:40 (by volume) (8 liters) the latter
  12. custombeing collected
  13. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8cedccdcd3be478d8bead8d2f831395f
Source dataset
uspto-grants-1982_12
Patent number
US04365062

Reaction notes

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