Hydrochloric Acid → HCID 13890975, compound

HRID 1382234Notes

Reaction equation

HRID 1382234 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:21](O)=[O:22])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH3:20])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:25]([O:27][C:28](=[O:35])[C@@H:29]([CH2:31][CH2:32][S:33][CH3:34])[NH2:30])[CH3:26].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.C(N(CC)CC)C>[CH2:25]([O:27][C:28](=[O:35])[C@@H:29]([CH2:31][CH2:32][S:33][CH3:34])[NH:30][C:21](=[O:22])[C@@H:9]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH3:20])[CH:12]=1)[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH3:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 6992941Ethyl D-methioninateHCID 13821420HCID 13821420, compound

Product 1

HCID 13890975HCID 13890975, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

To a suspension of N-tert-butoxycarbonyl-1-methyl-D-tryptophan (1.60 g) and hydrochloric acid salt of D-methionine ethyl ester (1.06 g) in dry methylene chloride (30 ml) which was cooled on an ice bath and stirred was added a solution of triethylamine (0.50 g) in dry methylene chloride (10 ml). The mixture was stirred for 30 minutes, and to the mixture was added a solution of N,N'-dicyclohexylcarbodiimide (1.04 g) in dry methylene chloride (10 ml). The resulting mixture was stirred overnight. After removal of the solvent, crude residue was taken up with a mixture of ethyl acetate and water, filtered, and organic layer was washed with 10% hydrochloric acid and saturated sodium bicarbonate solution, dried over magnesium sulfate, and evaporated to give crystalline N-tert-butoxycarbonyl-1-methyl-D-tryptophyl-D-methionine ethyl ester (2.43 g).

Workup

  1. temperaturewas cooled on an ice bath
  2. stirringThe mixture was stirred for 30 minutes
  3. stirringThe resulting mixture was stirred overnight
  4. customAfter removal of the solvent, crude residue
  5. additionwas taken up with a mixture of ethyl acetate and water
  6. filtrationfiltered
  7. washorganic layer was washed with 10% hydrochloric acid and saturated sodium bicarbonate solution
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-af0f2116c2d743ccaf553c4b3b83ae7e
Source dataset
uspto-grants-1989_02
Patent number
US04806538

Reaction notes

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