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

HRID 2083842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2083842
[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]

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-aecfb805071744e5a65d5108de7461b4
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04086219

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