Hydrochloric Acid → HCID 14456866, compound

HRID 279780Notes

Reaction equation

HRID 279780 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[CH2:8][CH:7]1[C:11](OCC)=[O:12].Cl>CO>[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[CH:7]([CH2:11][OH:12])[CH2:8][C:9]1=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13505933HCID 13505933, compound

Product 1

HCID 14456866HCID 14456866, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

47.6 g (0.162 mole) of ethyl 1-(2,4-dimethoxybenzyl)-4-oxo-2-azetidine-carboxylate prepared according to paragraph e) of Example 1 are reacted with 12.4 g (0.327 moles) of sodium-[tetrahydro-borate(III)] in 200 ml of methanol under external ice-cooling. The reaction takes place within about half an hour. The solution is made neutral by adding diluted hydrochloric acid, the methanol is distilled off and the oil precipitated from the aqueous mixture is extracted five times with 50 ml of ethyl acetate each. The united ethyl acetate layers are dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated. Thus 39.1 g of 1-(2,4-dimethoxy-benzyl)-4-(hydroxymethyl)-2-azetidinone are obtained. Yield: 96%.

Workup

  1. temperaturecooling
  2. customwithin about half an hour
  3. distillationthe methanol is distilled off
  4. customthe oil precipitated from the aqueous mixture
  5. extractionis extracted five times with 50 ml of ethyl acetate each
  6. dry with materialThe united ethyl acetate layers are dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-0929127b37cc44739dd55024c379bfb6
Source dataset
uspto-grants-1986_05
Patent number
US04587049

Reaction notes

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