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4-Methylmorpholine → N-t-butoxycarbonyl-L-tyrosylglycyl-L-alanine benzyl ester

HRID 436955
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 436955
ClC1C=C(Cl)C(Cl)=CC=1O[C:11](=[O:29])[C@H:12]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].Cl.[CH2:31]([O:38][C:39](=[O:47])[C@H:40]([CH3:46])[NH:41][C:42](=[O:45])[CH2:43][NH2:44])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CN1CCOCC1>C(Cl)Cl>[CH2:31]([O:38][C:39](=[O:47])[C@H:40]([CH3:46])[NH:41][C:42](=[O:45])[CH2:43][NH:44][C:11](=[O:29])[C@H:12]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=1)[NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1
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Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 13273165(2,4,5-trichlorophenyl) (2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoateHCID 53328828Benzyl glycyl-L-alaninate hydrochloride

Produkt 1

HCID 53750798N-t-butoxycarbonyl-L-tyrosylglycyl-L-alanine benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A solution of 17.6 parts N-t-butoxycarbonyl-L-tyrosine 2,4,5-trichlorophenyl ester, 9.0 parts glycyl-L-alanine benzyl ester hydrochloride and 1.2 parts N-methylmorpholine in 200 parts methylene chloride is stirred for 16 hours at room temperature. Removal of the solvent under reduced pressure affords a crude product which is purified by low pressure column chromatography to give N-t-butoxycarbonyl-L-tyrosylglycyl-L-alanine benzyl ester. The purified material is dissolved in 400 parts methanol. Then, 0.4 part palladium black metal catalyst is added and the mixture shaken with hydrogen at atmospheric pressure and room temperature for about 5 hours. The catalyst is removed by filtration, and the solvent is removed by evaporation under reduced pressure. The resulting material is purified by low-pressure chromatography to give N-t-butoxycarbonyl-L-tyrosylglycyl-L-alanine. This compound is represented by the following formula

Aufarbeitung

  1. customRemoval of the solvent under reduced pressure
  2. customaffords a crude product which
  3. customis purified by low pressure column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7dd09a1cefae4b53a49903cf89014486
Quelldatensatz
uspto-grants-1977_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04028319

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