4-Methylmorpholine → N-benzyloxycarbonyl-L-leucinamide

HRID 36509

Reaction equation

HRID 36509 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H](C(O)=O)CC(C)C)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N:21]1[CH2:26][CH2:25][O:24]CC1.[CH2:27](OC(Cl)=O)[CH:28]([CH3:30])[CH3:29].N.CO>C(Cl)Cl>[C:1]1([CH2:7][O:8][C:9]([NH:11][C:25](=[O:24])[C@H:26]([CH2:27][CH:28]([CH3:30])[CH3:29])[NH2:21])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 21705897Ammonia methanol

Product 1

HCID 69952024N-benzyloxycarbonyl-L-leucinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(phenylmethoxy)carbonyl]-L-leucine (3 g., 11.3 mmol.) in 60 mL of methylene chloride at -20° under argon was added N-methylmorpholine (1.24 mL, 11.3 mmol.) followed by isobutylchloroformate (1.47 mL, 11.3 mmol.). The resulting suspension was stirred at -20° C. for 15 minutes at which time a solution of ammonia/methanol (about 5.6M, 20 mL, 113 mmol.) was added. After 30 minutes at -20° C., the reaction was quenched with water and warmed to room temperature. The layers were separated and the aqueous layer was extracted with methylene chloride (2 x). The combined organic extracts were dried (MgSO4) and evaporated to give 2.82 g. of the title A compound.

Workup

  1. additionwas added
  2. customthe reaction was quenched with water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with methylene chloride (2 x)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customevaporated
  7. customto give 2.82 g

Sources & evidence

ORD record
ord-3d848cf5661e4511be75349638e4c970
Source dataset
uspto-grants-1995_05
Patent number
US05414013

Linked notes

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