Dicyclohexylcarbodiimide → HCID 53775475, compound

HRID 974864Notes

Reaction equation

HRID 974864 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:23][NH:24][CH:25]([C:36]([OH:38])=O)[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ON1C(=O)CCC1=O.Cl.[NH2:48][C@H:49]([C:52]([O:54][CH3:55])=[O:53])[CH2:50][OH:51]>O1CCOCC1.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:16]([O:23][NH:24][CH:25]([C:36]([NH:48][C@H:49]([C:52]([O:54][CH3:55])=[O:53])[CH2:50][OH:51])=[O:38])[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 19969586HCID 19969586, compound

Product 1

HCID 53775475HCID 53775475, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

1.24 g of dicyclohexylcarbodiimide was added to 30 ml Of a solution of 1.77 g of N-benzyloxy-DL-tryptophane and 0.70 g of N-hydroxysuccinimide in anhydrous dioxane, with ice-cooling. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered to remove the insoluble materials, whereby a light brown solution was obtained. Separately, 0.8 ml of triethylamine was added to 20 ml of a suspension of 0.89 g of methyl L-serinate hydrochloride in anhydrous dioxane. The mixture was stirred at room temperature for 2 hours. Thereto was added the above light brown solution. The resulting mixture was stirred at room temperature for 66 hours. The reaction mixture was diluted with 200 ml of ethyl acetate. The resulting solution was washed with 1N hydrochloric acid and an aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent, to obtain 2.07 g of methyl (N-benzyloxy-DL-tryptophyl)-L-serinate as a brown oily substance.

Workup

  1. temperaturecooling
  2. filtrationThe reaction mixture was filtered
  3. customto remove the insoluble materials, whereby a light brown solution
  4. customwas obtained
  5. stirringThe mixture was stirred at room temperature for 2 hours
  6. additionThereto was added the above light brown solution
  7. stirringThe resulting mixture was stirred at room temperature for 66 hours
  8. washThe resulting solution was washed with 1N hydrochloric acid
  9. dry with materialan aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate
  10. distillationsubjected to distillation
  11. customto remove the solvent

Sources & evidence

ORD record
ord-2ccf01636dab4380869122c86885e562
Source dataset
uspto-grants-1997_03
Patent number
US05607934

Reaction notes

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