1-Hydroxybenzotriazole → N-(Morpholinocarbonyl)-L-phenylalanine S-methyl-L-cysteine methyl ester

HRID 1087313

Reaktionsgleichung

Reaktionsgleichung von HRID 1087313
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])[CH2:3][CH2:2]1.[CH3:21][O:22][C:23](=[O:29])[C@H:24]([CH2:26][S:27][CH3:28])[NH2:25].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C(OCC)(=O)C.C(N(CC)CC)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:8])[CH2:3][CH2:2]1.[CH3:21][O:22][C:23](=[O:29])[C@H:24]([CH2:26][S:27][CH3:28])[NH2:25]

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 664657CP 84364HCID 1277655Methyl (2R)-2-amino-3-(methylsulfanyl)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 67865905N-(Morpholinocarbonyl)-L-phenylalanine S-methyl-L-cysteine methyl esterAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 0.96 g N-(morpholinocarbonyl)-L-phenylalanine 3 and 0.55 g S-methyl-L-cysteine methyl ester in 50 mL anhydrous methylene chloride at ambient temperature was added 0.50 mL triethylamine, 0.51 g 1-hydroxybenzotriazole and 0.70 g 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride. After being stirred for 4 h, the solution was diluted with 100 mL ethyl acetate and was washed with 2×35 mL 0.1N hydrochloric acid solution and 2×35 mL 0.1N sodium hydroxide solution. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to afford 1.15 g of the desired solid dipeptide.

Aufarbeitung

  1. washwas washed with 2×35 mL 0.1N hydrochloric acid solution and 2×35 mL 0.1N sodium hydroxide solution
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9f93c1358bdf4432a0b26833ddc82d78
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05034376

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