benzhydryl (E)-(2S,3S,5R)-3-(2-formyl-vinyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate → benzhydryl (E)-(2S,3S,5R)-3-(3-hydroxy-propenyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

5.80 g (14.2 mmol) of benzhydryl (E)-(2S,3S,5R)-3-(2-formyl- vinyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 240 ml of toluene under argon and cooled to 0° C. Then, 14.2 ml (21.3 mmol) of a 20% diisobutyl-aluminium hydride solution (in toluene) were added dropwise and the cooling bath is removed. The reaction mixture was stirred at room temperature for 6 hours, poured into 150 ml of saturated ammonium chloride solution and extracted three times with 200 ml of methylene chloride each time. The combined organic extracts were washed once with 300 ml of water as well as saturated sodium chloride solution, dried over magnesium sulfate, filtered and freed from solvent on a rotary evaporator. The residual yellow oil was chromatographed over silica gel (particle size 0.040-0.063 mm) with ethyl acetate:n-hexane (9:16) as the eluent. Yield: 1.90 g (32%) of colorless resin IR (film): 3480(br), 1778, 1750, 1202, 1080, 988 cm-1MS: (M+NH4)+ 427.6

1. customthe cooling bath is removed
2. additionpoured into 150 ml of saturated ammonium chloride solution
3. extractionextracted three times with 200 ml of methylene chloride each time
4. washThe combined organic extracts were washed once with 300 ml of water as well as saturated sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customfreed from solvent on a rotary evaporator
8. customThe residual yellow oil was chromatographed over silica gel (particle size 0.040-0.063 mm) with ethyl acetate:n-hexane (9:16) as the eluent

ORD record

ord-17cb7501c88545299286529c1f3651d1

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05644053