Hydrochloric Acid → HCID 57108405, compound

HRID 1252203Notes

Reaction equation

HRID 1252203 reaction equation
[CH2:1]([CH:10]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[N:11]1[CH:14]([O:15][C:16](=[O:18])[CH3:17])[CH:13]([CH:19]=[CH2:20])[C:12]1=[O:21])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.[O:34]1CCCC1>O.[OH-].[Na+].C(OCC)C>[CH2:22]([CH:10]([CH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[N:11]1[CH:14]([O:15][C:16](=[O:18])[CH3:17])[CH:13]([CH:19]([OH:34])[CH3:20])[C:12]1=[O:21])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 57078408HCID 57078408, compound

Product 1

HCID 57108405HCID 57108405, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

A solution of 1-(di-p-anisylmethyl)-3-ethenyl-4-acetoxy-2-azetidinone (3.80 g) and mercuric acetate (3.20 g) in tetrahydrofuran (10 ml) and water (4 ml) was stirred for 1 hour at room temperature. The reaction mixture was treated with 1N sodium hydroxide (9 ml) at 0° C. and then a solution of sodium borohydride (0.4 g) in 1N aqueous sodium hydroxide. After stirring at the same temperature for 5 to 6 minutes, the reaction mixture was neutralized with dilute hydrochloric acid, diluted with diethyl ether and filtered to remove any insoluble materials over Cerite. The filtrate was extracted with diethyl ether and the ether extract was washed successively with aqueous sodium bicarbonate and water, dried over anhydrous sodium sulfate and evaporated to give an oily residue which was then purified by silica gel chromatography to give 1-(di-p-anisylmethyl)-3-(1-hydroxyethyl)-4-acetoxy-2-azetidinone.

Workup

  1. filtrationfiltered
  2. customto remove any insoluble materials over Cerite
  3. extractionThe filtrate was extracted with diethyl ether
  4. extractionthe ether extract
  5. washwas washed successively with aqueous sodium bicarbonate and water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customto give an oily residue which
  9. customwas then purified by silica gel chromatography

Sources & evidence

ORD record
ord-5e9e9d958de04f90a3815f719e4ef29a
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

Loading…