Dicyclohexylcarbodiimide → Carbobenzyloxytryptophylserine methyl ester

HRID 1763731

Reaktionsgleichung

Reaktionsgleichung von HRID 1763731
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].[CH2:10]([O:17][C:18]([NH:20][C@H:21]([C:32](O)=[O:33])[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(N(CC)CC)C.CN(C)C=O>[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH:6][C:32](=[O:33])[C@H:21]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[NH:20][C:18]([O:17][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:19]

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 101176benzyloxycarbonyl-L-tryptophanHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Produkt 1

HCID 12821032Carbobenzyloxytryptophylserine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

L-Serine methyl ester hydrochloride, 5 g., is dissolved in 75 ml. of dimethylformamide and the solution cooled in an ice bath. Triethylamine, 4.9 ml., is added then 11.9 g. of Nα -benzyloxycarbonyl-L-tryptophan, 5.25 g. of 1-hydroxybenztriazole and finally 8.0 g. of dicyclohexylcarbodiimide. The reaction is stirred with ice bath cooling overnight, allowing the temperature to rise to room temperature, then an additional twenty-four hours at room temperature. The mixture is filtered and the solid washed with dimethylformamide. The filtrate is evaporated under reduced pressure and the residue dissolved in ethyl acetate and washed with dilute hydrochloric acid, saturated salt solution, three times with 5% sodium bicarbonate solution, saturated salt solution, and finally with water. The ethyl acetate solution is then dried over magnesium sulfate and evaporated. The residue is crystallized from 250 ml. of benzene and then from ethyl acetate and petroleum ether; 12.5 g.; m.p. 133°-135° C.; [α]D23 -12.4° (c 2, methanol); ultraviolet in methanol λmax 290 E11 115; λmax 281 E11 131; λmax 274 E11 122.

Aufarbeitung

  1. dissolution, is dissolved in 75 ml
  2. addition, is added
  3. temperaturecooling overnight
  4. customto rise to room temperature
  5. customan additional twenty-four hours
  6. customat room temperature
  7. filtrationThe mixture is filtered
  8. washthe solid washed with dimethylformamide
  9. customThe filtrate is evaporated under reduced pressure
  10. dissolutionthe residue dissolved in ethyl acetate
  11. washwashed with dilute hydrochloric acid, saturated salt solution, three times with 5% sodium bicarbonate solution, saturated salt solution
  12. dry with materialThe ethyl acetate solution is then dried over magnesium sulfate
  13. customevaporated
  14. customThe residue is crystallized from 250 ml

Quellen und Nachweise

ORD-Eintrag
ord-99785dc6ae3c4c05a4d7a562038650bd
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04111923

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