4-Methylmorpholine → HCID 21392364, compound

HRID 461793Notes

Reaction equation

HRID 461793 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([OH:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].CN1CCOCC1.[C:20](Cl)([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>C(Cl)Cl>[CH2:23]([O:22][C:20]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([OH:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 10387Benzyl chloroformateHCID 21392341HCID 21392341, compound

Product 1

HCID 21392364HCID 21392364, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well stirred mixture of 0.05 moles of ethyl 6-amino-2-hydroxyhexanoate and 100 ml of methylene chloride which has been cooled to 0° to 5° C is added 0.1 moles of N-methylmorpholine followed by 0.055 moles of carbobenzoxy chloride. The reaction mixture is stirred for 1 hour then washed with saturated sodium bicarbonate solution. The organic layer is dried over sodium sulfate and concentrated in vacuo. Chromatography of the residue on silica gel and elution with methanol/chloroform gives ethyl 6-(benzyloxycarbonylamino)-2-hydroxyhexanoate.

Workup

  1. temperaturehas been cooled to 0° to 5° C
  2. stirringThe reaction mixture is stirred for 1 hour
  3. washthen washed with saturated sodium bicarbonate solution
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. washChromatography of the residue on silica gel and elution with methanol/chloroform

Sources & evidence

ORD record
ord-05e2e740334f4fb2b1c5efd3168b779e
Source dataset
uspto-grants-1977_12
Patent number
US04064236

Reaction notes

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