Dicyclohexylcarbodiimide → Nalpha-[N-t-Butoxycarbonyl-3-(2-pyridyl)-D-alanyl]-1,beta-dimethyl-D-tryptophan methyl ester

HRID 1382247Notes

Reaction equation

HRID 1382247 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([C@H:6]([CH3:17])[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH3:16])[CH:8]=1)[NH2:5].[C:19]([O:23][C:24]([NH:26][C@@H:27]([C:35](O)=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([CH:6]([CH3:17])[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH3:16])[CH:8]=1)[NH:5][C:35](=[O:36])[C@@H:27]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[NH:26][C:24]([O:23][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:25]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 7019139(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(pyridin-2-yl)propanoic acidHCID 14151960(alphaR,betaR)-1,beta-dimethyltryptophan methyl ester

Product 1

HCID 22841452Nalpha-[N-t-Butoxycarbonyl-3-(2-pyridyl)-D-alanyl]-1,beta-dimethyl-D-tryptophan methyl esterYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (αR,βR)-1,β-dimethyltryptophan methyl ester (6.36 g) and Nα -t-butoxycarbonyl-3-(2-pyridyl)-D-alanine (6.65 g) in dry methylene chloride (250 ml) was added dicyclohexylcarbodiimide (5.15 g), and resulting mixture was stirred for 1.5 hours at room temperature. After evaporation of the solvent, crude residue was taken up with ethyl acetate (200 ml), filtered, washed with water and saturated sodium bicarbonate solution, dried over magnesium sulfate, treated with active charcoal, and evaporated. Nα -[N-t-Butoxycarbonyl-3-(2-pyridyl)-D-alanyl]-1,β-dimethyl-D-tryptophan methyl ester (10.54 g) was obtained as an oil.

Workup

  1. customresulting mixture
  2. customAfter evaporation of the solvent, crude residue
  3. filtrationfiltered
  4. washwashed with water and saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with active charcoal
  7. customevaporated

Sources & evidence

ORD record
ord-db28e4ba75924fbf8815ec032c9677f0
Source dataset
uspto-grants-1989_02
Patent number
US04806538

Reaction notes

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