Water → HCID 53791026, compound

HRID 1649265Notes

Reaction equation

HRID 1649265 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH:12]([O:25][C:26]([C:28]1[N:29]2[CH:32]([S:33][CH2:34][C:35]=1[CH2:36][CH:37]=[O:38])[CH:31]([NH:39][C:40](=[O:79])[C:41](=[N:67][O:68][C:69]([C:72]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])=[O:73])([CH3:71])[CH3:70])[C:42]1[N:43]=[C:44]([NH:47][C:48]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[S:45][CH:46]=1)[C:30]2=[O:80])=[O:27])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>N1C=CC=CC=1>[CH:12]([O:25][C:26]([C:28]1[N:29]2[CH:32]([S:33][CH2:34][C:35]=1[CH:36]=[CH:37][O:38][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH:31]([NH:39][C:40](=[O:79])[C:41](=[N:67][O:68][C:69]([C:72]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])=[O:73])([CH3:70])[CH3:71])[C:42]1[N:43]=[C:44]([NH:47][C:48]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[S:45][CH:46]=1)[C:30]2=[O:80])=[O:27])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 54127599HCID 54127599, compound2×

Product 1

HCID 53791026HCID 53791026, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

p-Toluenesulphonyl chloride (1.31 g) is added to a solution, cooled to 5° C., of the syn isomer of 2-benzhydryloxycarbonyl-7-{2-[(2-t-butoxycarbonylprop-2-yl)-oxyimino]-2-(2-tritylaminothiazol-4-yl)-acetamido}-3-formylmethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (product 5e) (4.45 g) in pyridine (50 cc). The temperature is left to rise to 20° C. in the course of 30 minutes, the mixture is stirred for 1 hour at 20° C. and poured into iced water (300 cc), the water is decanted and the insoluble pasty product is taken up in ethyl acetate (300 cc). The solution is washed with 1 N hydrochloric acid (100 cc), a saturated solution of sodium bicarbonate (100 cc) and a saturated solution of sodium chloride (100 cc), dried over sodium sulphate and filtered and the filtrate is concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa). The product thus obtained is used as such for the remainder of the synthesis. This product (1 g) is purified by chromatography on a column of silica gel (0.05-0.2) (20 g) (diameter of the column: 1.7 cm), elution being carried out with an 80/20 (by volume) mixture of cyclohexane and ethyl acetate, and 50 cc fractions being collected. Fractions 4 to 12, containing the pure product, are evaporated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. to give a product (5d) (0.43 g), which is a mixture of the E and Z forms (in proportions--determined by NMR--of 75% of the E form and 25% of the Z form), in the form of a pale yellow solid.

Workup

  1. waitThe temperature is left
  2. customto rise to 20° C. in the course of 30 minutes
  3. customthe water is decanted
  4. washThe solution is washed with 1 N hydrochloric acid (100 cc)
  5. dry with materiala saturated solution of sodium bicarbonate (100 cc) and a saturated solution of sodium chloride (100 cc), dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)
  8. customThe product thus obtained
  9. customsuch for the remainder of the synthesis
  10. customThis product (1 g) is purified by chromatography on a column of silica gel (0.05-0.2) (20 g) (diameter of the column
  11. wash1.7 cm), elution
  12. additionbeing carried out with an 80/20 (by volume) mixture of cyclohexane and ethyl acetate, and 50 cc fractions
  13. custombeing collected
  14. additionFractions 4 to 12, containing the pure product
  15. customare evaporated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C.

Sources & evidence

ORD record
ord-f79621ed02774e1b902ae2367bcc864f
Source dataset
uspto-grants-1983_11
Patent number
US04415562

Reaction notes

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