Leucine, N-carboxy-, N-benzyl ester, L- → HCID 54133509, compound

HRID 1982648Notes

Reaction equation

HRID 1982648 reaction equation
[C:1]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][CH:14]([CH3:16])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].O.ON1C2C=CC=CC=2N=N1.[CH3:31][C:32]([O:35][C:36](=[O:39])[CH2:37][NH2:38])([CH3:34])[CH3:33]>C(#N)C.O1CCCC1.O1CCCC1>[C:1]([NH:11][C@H:12]([C:17]([NH:38][CH2:37][C:36]([O:35][C:32]([CH3:34])([CH3:33])[CH3:31])=[O:39])=[O:19])[CH2:13][CH:14]([CH3:15])[CH3:16])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

6

Reactant 3

HCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 151417Glycine tert-butyl esterHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 54133509HCID 54133509, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

To a cold solution of 5.00 g of carbobenzoxy-L-leucine, 2.55 g of 1-hydroxybenzotriazole hydrate and 2.47 g of glycine 1,1-dimethylethyl ester in 100 ml of 1:1 acetonitrile/tetrahydrofuran is added dropwise a solution of 3.89 g of N,N-dicyclohexylcarbodiimide in 40 ml of tetrahydrofuran. The solution is stirred overnight allowing the ice bath to melt. The mixture is filtered and the solvent removed under reduced pressure. The residue is dissolved in ethyl acetate and washed with water, a 0.1M citric acid solution, a saturated sodium bicarbonate solution and then a saturated brine solution. After drying over magnesium sulfate, the solvent is removed under reduced pressure. The residue is chromatographed on silica gel eluting with 7:3 chloroform/ethyl acetate giving 6.68 g of an oil.

Workup

  1. filtrationThe mixture is filtered
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is chromatographed on silica gel eluting with 7:3 chloroform/ethyl acetate giving 6.68 g of an oil

Sources & evidence

ORD record
ord-9e07cfa6f0b240bb8937b215f1eb936d
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

Loading…