Hydrochloric Acid → 3,4-Morpholinedicarboxylic acid, 4-(2-propenyl) ester, (S)-

HRID 1029656Notes

Reaction equation

HRID 1029656 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][O:10][CH2:9][C@H:8]1[C:13]([O:15]CC)=[O:14])=[O:6])[CH:2]=[CH2:3].Cl>C(O)C.[OH-].[Na+]>[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][O:10][CH2:9][C@H:8]1[C:13]([OH:15])=[O:14])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15117290HCID 15117290, compound

Product 1

HCID 151172913,4-Morpholinedicarboxylic acid, 4-(2-propenyl) ester, (S)-Yield 100.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl (3S)-4-allyloxycarbonylmorpholine-3-carboxylate (5.90 g) in a mixture of ethanol (15 ml) and 4N aqueous sodium hydroxide (15 ml) was stirred at 30°-40° C. for one hour. Ethanol was evaporated to give an aqueous solution. The aqueous solution was adjusted to pH 2 with concentrated hydrochloric acid, extracted with ethyl acetate (100 ml), dried over magnesium sulfate, and evaporated under reduced pressure to give (3S)-4-allyloxycarbonylmorpholine-3-carboxylic acid (5.24 g) as a syrup.

Workup

  1. customEthanol was evaporated
  2. customto give an aqueous solution
  3. extractionextracted with ethyl acetate (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-52feb2d99825468d8c8c9890826f8472
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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