Methanol → HCID 53819756, compound

HRID 1706524Notes

Reaction equation

HRID 1706524 reaction equation
C1(=O)[N:5]([CH:6]2[CH2:9][N:8]([CH:10]([C:17]([O:19][CH3:20])=[O:18])[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]2=[O:21])C(=O)C2=CC=CC=C12.CN(C)CCCN.CO>C(Cl)(Cl)Cl>[NH2:5][CH:6]1[CH2:9][N:8]([CH:10]([C:17]([O:19][CH3:20])=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]1=[O:21]

Participants

5

Reactant 3

HCID 887MethanolHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 13942931HCID 13942931, compound

Product 1

HCID 53819756HCID 53819756, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Phthalimido-1-(α-methoxycarbonylbenzyl)-2-azetidinone (0.36 g.) and N,N-dimethyl-1,3-propanediamine (0.22 g.) were added to a mixture of methanol (5 ml.) and chloroform (5 ml.), whereafter the mixture was stirred at ambient temperature for 18 hours. The reaction mixture was evaporated to dryness under reduced pressure, and ethyl acetate (20 ml.) and water were poured into the residue obtained. The ethyl acetate layer was separated out from the mixture and the remaining aqueous layer was further extracted with ethyl acetate (10 ml.). The combined ethyl acetate solution was extracted with 1 N hydrochloric acid (3 ml.) and water (10 ml.) respectively. The combined aqueous extracts were adjusted to pH 8.6 with an aqueous sodium bicarbonate. The aqueous solution was extracted with two 10 ml. portions of ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by distillation from the solution under reduced pressure to give oily 3-amino-1-(α-methoxycarbonylbenzyl)-2-azetidinone (0.13 g.).

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure, and ethyl acetate (20 ml.) and water
  2. additionwere poured into the residue
  3. customobtained
  4. customThe ethyl acetate layer was separated out from the mixture
  5. extractionthe remaining aqueous layer was further extracted with ethyl acetate (10 ml.)
  6. extractionThe combined ethyl acetate solution was extracted with 1 N hydrochloric acid (3 ml.) and water (10 ml.) respectively
  7. extractionThe aqueous solution was extracted with two 10 ml
  8. washThe combined extracts were washed with saturated aqueous sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was removed by distillation from the solution under reduced pressure

Sources & evidence

ORD record
ord-b0eb25588737445b983570213d8df0ca
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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