4-Methylmorpholine → HCID 54230031, compound

HRID 1589301Notes

Reaction equation

HRID 1589301 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:27])[C@H:21]([CH2:23][CH:24]([CH3:26])[CH3:25])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Br[CH:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31].CN1CCOCC1>C(#N)C>[CH2:12]([O:19][C:20](=[O:27])[C@H:21]([CH2:23][CH:24]([CH3:25])[CH3:26])[NH:22][C@@H:29]([C:30]([O:32][CH3:33])=[O:31])[CH3:34])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 95576Methyl 2-bromopropionateHCID 6451312L-Leucine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 54230031HCID 54230031, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Leucine benzyl ester para-toluene sulphonic acid salt (113 g) in dry acetonitrile (800 ml) was treated with methyl 2-bromopropionate (62.7 ml) and N-methyl morpholine (100 ml) under reflux for 16 h. The reaction mixture was concentrated in vacuo and the residue in ethyl acetate washed with brine, dried (Na2SO4) and evaporated. Chromatography of the resulting oil on silica in 1:4 ethyl acetate-hexane gave N-[1-(R)-methoxycarbonylethyl]-L-leucine benzyl ester (45 g) as the faster running fraction. This material was treated exactly as described above in Example 2 to give the title compound.

Workup

  1. temperatureunder reflux for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. washthe residue in ethyl acetate washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-cd6b7e2fd21e41fbb5f672d71211e481
Source dataset
uspto-grants-1986_02
Patent number
US04568666

Reaction notes

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