Hydrochloric Acid → HCID 13175940, compound

HRID 2413413Notes

Reaction equation

HRID 2413413 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH:25](Br)[CH:26]=O)[CH:20]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:19]2=[O:37])=[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.[C:38]([NH2:46])(=[S:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CS(Cl)(=O)=O.Cl>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[C:25]1[S:45][C:38]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[N:46][CH:26]=1)[CH:20]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:19]2=[O:37])=[O:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 683563ThiobenzamideHCID 13175928HCID 13175928, compound

Product 1

HCID 13175940HCID 13175940, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 2-benzhydryloxycarbonyl-3-(1-bromo-2-oxoethyl)-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (a mixture of the bromoaldehyde epimers) (5.87 g) and thiobenzamide (1.5 g) in dry tetrahydrofuran (60 cc) is stirred at 20° C. for 1 hour 20 minutes, and thereafter there are added to the reaction mixture, cooled to 2° C., methanesulphonyl chloride (0.85 cc) followed, in 5 minutes, by triethylamine (5.6 cc). After having been stirred for 2 hours at 2° C., the reaction mixture is poured into a mixture of ethyl acetate (100 cc) and 1N hydrochloric acid (50 cc). The organic phase is washed with a saturated sodium bicarbonate solution (100 cc) and then with a saturated sodium chloride solution (100 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. The residue is chromatographed on a column (height: 25 cm; diameter: 5 cm) of silica gel (0.04-0.06 mm), elution being carried out under a pressure of 0.4 bar (40 kPa) with an 80:20 (by volume) mixture of cyclohexane and ethyl acetate, and 125 cc fractions being collected. Fractions 17 to 22, containing the pure product, are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. 2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-(2-phenyl-thiazol-5-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1 g) is obtained in the form of a yellow froth.

Workup

  1. additionthere are added to the reaction mixture
  2. temperaturecooled to 2° C.
  3. stirringAfter having been stirred for 2 hours at 2° C.
  4. washThe organic phase is washed with a saturated sodium bicarbonate solution (100 cc)
  5. dry with materialwith a saturated sodium chloride solution (100 cc), dried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C
  7. customThe residue is chromatographed on a column (height: 25 cm; diameter: 5 cm) of silica gel (0.04-0.06 mm), elution
  8. additionbeing carried out under a pressure of 0.4 bar (40 kPa) with an 80:20 (by volume) mixture of cyclohexane and ethyl acetate, and 125 cc fractions
  9. custombeing collected
  10. additionFractions 17 to 22, containing the pure product
  11. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C

Sources & evidence

ORD record
ord-a27650603b2348f7b6d03528a3b70385
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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