Dicyclohexylcarbodiimide → CARBOBENZYLOXY-L-ISOLEUCYL-L-TRYPTOPHAN METHYL ESTER

HRID 2083842Notes

Reaction equation

HRID 2083842 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=O)[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:21][O:22][C:23](=[O:36])[C@H:24]([CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)[NH2:25].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CO.C(N(CC)CC)C.CN(C)C=O>[CH3:21][O:22][C:23](=[O:36])[C@H:24]([CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)[NH:25][C:17](=[O:19])[C@H:12]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724772N-[(Phenylmethoxy)carbonyl]-L-isoleucineHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 21074402CARBOBENZYLOXY-L-ISOLEUCYL-L-TRYPTOPHAN METHYL ESTER

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Nα -Benzyloxycarbonyl-L-isoleucine, 2.65 g., and 2.54 g. of L-tryptophan methyl ester hydrochloride are dissolved in 30 ml. of dimethylformamide and cooled in an ice bath. Triethylamine, 1.4 ml., is added and then 1.5 g. of 1-hydroxy-benzotriazole. Lastly 2.3 g. of dicyclohexylcarbodiimide is added and the reaction let warm to room temperature with stirring continued for 40 hours. The mixture is filtered and the solvent evaporated. The residue is dissolved in 150 ml. of ethyl acetate and washed with 0.5 N hydrochloric acid, saturated sodium chloride solution, 5% sodium bicarbonate solution and finally with saturated sodium chloride solution. The ethyl acetate solution is dried over magnesium sulfate, filtered and the solution evaporated. The product is crystallized from methanol-ether-hexane to give 2.58 g. of the above named product, mp. 152°-155° C; [α]D23 -16.6° (c 1.95, methanol).

Workup

  1. addition, is added
  2. filtrationThe mixture is filtered
  3. customthe solvent evaporated
  4. dissolutionThe residue is dissolved in 150 ml
  5. washof ethyl acetate and washed with 0.5 N hydrochloric acid, saturated sodium chloride solution, 5% sodium bicarbonate solution and finally with saturated sodium chloride solution
  6. dry with materialThe ethyl acetate solution is dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solution evaporated
  9. customThe product is crystallized from methanol-ether-hexane
  10. customto give 2.58 g

Sources & evidence

ORD record
ord-aecfb805071744e5a65d5108de7461b4
Source dataset
uspto-grants-1978_04
Patent number
US04086219

Reaction notes

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