Potassium Hydroxide → HCID 56615901, compound

HRID 2290991Notes

Reaction equation

HRID 2290991 reaction equation
Cl[C@H:2]1[C@@H:5]([C@@H:6]2[CH2:10][O:9][C:8]([CH3:12])([CH3:11])[O:7]2)[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])[C:3]1=[O:24].[OH-].[K+]>CO.[Pd]>[CH3:23][O:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH2:13][N:4]1[C@H:5]([C@@H:6]2[CH2:10][O:9][C:8]([CH3:12])([CH3:11])[O:7]2)[CH2:2][C:3]1=[O:24]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 56624269HCID 56624269, compound

Product 1

HCID 56615901HCID 56615901, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4.26 g (12.0 mmol) of (3S,4R)-3-chloro-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone and 3 g (53 mmol) of potassium hydroxide in 50 ml of methanol is hydrogenated in the presence of 400 mg of 5 percent palladium/carbon for 1 hour at normal pressure. The catalyst is filtered off, the filtrate is diluted with ethyl acetate and washed with 1M phosphate buffer (pH 7) and saturated sodium chloride solution. The organic phase is dried over sodium sulphate and evaporated, whereupon the residue is chromatographed on silica gel with ethyl acetate/hexane as the eluent. After two-fold crystallization from methylene chloride/hexane there is obtained (S)-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone as white crystals of melting point 85°-86°; [α]D20 =+50.3° (c=1, chloroform).

Workup

  1. filtrationThe catalyst is filtered off
  2. additionthe filtrate is diluted with ethyl acetate
  3. washwashed with 1M phosphate buffer (pH 7) and saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. customevaporated, whereupon the residue
  6. customis chromatographed on silica gel with ethyl acetate/hexane as the eluent
  7. customAfter two-fold crystallization from methylene chloride/hexane there

Sources & evidence

ORD record
ord-ef4e2ccfc4e2467eba1fe42a0aa71559
Source dataset
uspto-grants-1986_10
Patent number
US04619787

Reaction notes

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