Hydrochloric Acid → HCID 15117278, compound

HRID 1029653Notes

Reaction equation

HRID 1029653 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][S:10][CH2:9][CH:8]1[C:13]([O:15]CC)=[O:14])=[O:6])[CH:2]=[CH2:3].CO.O1CCCC1.Cl>[OH-].[Na+]>[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][S:10][CH2:9][CH:8]1[C:13]([OH:15])=[O:14])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 15117277HCID 15117277, compound

Product 1

HCID 15117278HCID 15117278, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 4-(allyloxycarbonyl)thiomorpholine-3-carboxylate (15.4 g) in a mixture of 4N aqueous sodium hydroxide (30 ml), methanol (30 ml) and tetrahydrofuran (75 ml) was refluxed for 90 minutes. The organic solvents were evaporated to give an aqueous solution. The aqueous solution was adjusted to pH 2 with concentrated hydrochloric acid, extracted with ethyl acetate (200 ml), dried over magnesium sulfate, and evaporated under reduced pressure to give 4-(allyloxycarbonyl)thiomorpholine-3-carboxylic acid (14.0 g) as a syrup.

Workup

  1. temperaturewas refluxed for 90 minutes
  2. customThe organic solvents were evaporated
  3. customto give an aqueous solution
  4. extractionextracted with ethyl acetate (200 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9e47cc89a9534ed0956a2f6806f965df
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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