4-Methylmorpholine → N-benzyloxycarbonyl-L-leucinamide

HRID 412100

Reaction equation

HRID 412100 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H](C(O)=O)CC(C)C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:21]1[CH2:26][CH2:25][O:24]CC1.ClC(O[CH2:31][CH:32]([CH3:34])[CH3:33])=O>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C:25](=[O:24])[C@H:26]([CH2:31][CH:32]([CH3:34])[CH3:33])[NH2:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 74840Leucine, N-carboxy-, N-benzyl ester, L-

Product 1

HCID 69952024N-benzyloxycarbonyl-L-leucinamideYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of N-benzyloxycarbonyl-L-leucine (4.6 g, 17.3 mmol) in THF, cooled to −40° C., was added N-methylmorpholine (3.68 g, 36.4 mmol; 4.0 mL) and isobutyl chloroformate (2.37 g, 17.3 mmol; 2.25 mL). After stirring for 15 min, ammonia was bubbled through the solution for 5 min. The solution was warmed to room temperature, evaporated, and the residue was dissolved in ethyl acetate, washed with 0.1 N Hcl, and saturated brine, then dried (MgSO4), filtered and evaporated to dryness to give the title compound as a white solid (4.58 g, 100%).

Workup

  1. customammonia was bubbled through the solution for 5 min
  2. customevaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with 0.1 N Hcl, and saturated brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-41ade019f79e49509addeb7918d5d1ee
Source dataset
uspto-grants-2003_05
Patent number
US06562842B2

Linked notes

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