4-Methylmorpholine → N-[N2-[(1,1-dimethylethoxy) carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysinyl]-L-alanine 1,1-dimethylethyl ester

HRID 34492

Reaktionsgleichung

Reaktionsgleichung von HRID 34492
CN1CCOCC1.[CH3:8][C:9]([O:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH2:15])([CH3:11])[CH3:10].N#N.[CH3:20][C:21]([CH3:46])([O:23][C:24]([NH:26][C@H:27]([C:43](O)=[O:44])[CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])=[O:25])[CH3:22].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>ClCCl>[CH3:8][C:9]([O:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH:15][C:43](=[O:44])[C@H:27]([CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:34])[NH:26][C:24]([O:23][C:21]([CH3:46])([CH3:20])[CH3:22])=[O:25])([CH3:11])[CH3:10]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 89016L-Alanine 1,1-dimethylethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86742311N2 [(1,1-dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine

Produkt 1

HCID 53963310N-[N2-[(1,1-dimethylethoxy) carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysinyl]-L-alanine 1,1-dimethylethyl esterAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-Methylmorpholine (3.3 ml) was added to a suspension of L-alanine 1,1 -dimethylethyl ester (4.0 g), N2 -[(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine (11.4 g), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (5.8 g) and 1-hydroxybenzotriazole (4.1 g) in dichloromethane (150 ml). The resulting mixture was allowed to stand for 18 hours, and was then poured into distilled water (200 ml). The organic phase was separated, washed with water, saturated sodium hydrogen carbonate, dilute aqueous citric acid, brine and dried over anhydrous magnesium sulphate. The solvent was removed under reduced pressure to yield N-[N2 -[(1,1-dimethylethoxy) carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysinyl]-L-alanine 1,1-dimethylethyl ester (12.6 g) as a foam.

Aufarbeitung

  1. additionwas then poured
  2. distillationinto distilled water (200 ml)
  3. customThe organic phase was separated
  4. washwashed with water, saturated sodium hydrogen carbonate, dilute aqueous citric acid, brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-24498aec61e446009080dc62880529ac
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761483

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