4-Methylmorpholine → N-[1-(R)-methoxycarbonylethyl]-L-leucine benzyl ester

HRID 1980827Notes

Reaction equation

HRID 1980827 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 54230031N-[1-(R)-methoxycarbonylethyl]-L-leucine benzyl ester

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-25e4c01b84814f9e93ff530b376f06b7
Source dataset
uspto-grants-1985_04
Patent number
US04511504

Reaction notes

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