L-Proline 1,1-dimethylethyl ester → H-Lys(Boc)-Pro-OtBu

HRID 615660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 615660
C(OC([NH:11][C@H:12]([C:25]([N:27]1[CH2:38][CH2:37][CH2:36][C@H:28]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:26])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=O)C1C=CC=CC=1.N1CCC[C@H]1C(OC(C)(C)C)=O>[OH-].[OH-].[Pd+2].C(OCC)(=O)C.C(O)C>[CH3:23][C:21]([CH3:24])([O:20][C:18]([NH:17][CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]([C:25]([N:27]1[CH2:38][CH2:37][CH2:36][C@H:28]1[C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])=[O:26])[NH2:11])=[O:19])[CH3:22]

Komponenten

6

Edukt 2

HCID 6453108L-Proline 1,1-dimethylethyl esterHCID 14010667N-(Nalpha-benzyloxycarbonyl-Nepsilon-tert-butoxycarbonyl-L-lysyl)-L-proline tert-butyl ester

Produkt 1

HCID 14010669H-Lys(Boc)-Pro-OtBu

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of the 1,1-dimethylethyl ester product from part (a) (4.13 g., 7.73 mmole) and palladium hydroxide/carbon catalyst (400 mg.) in ethyl acetate (90 ml.) and ethanol (10 ml.) is stirred under a hydrogen atmosphere (balloon). The system is evacuated and refilled with fresh hydrogen every 30 minutes. After stirring for 3 hours, the catalyst is removed by filtration (Teflon millipore) and the filtrate is concentrated at reduced pressure to give 3.15 g. of 1-[N6 -](1,1-dimethylethoxy)carbonyl]-L-lysyl]-L-proline, 1,1-dimethylethyl ester as a colorless solid.

Aufarbeitung

  1. customThe system is evacuated
  2. additionrefilled with fresh hydrogen every 30 minutes
  3. stirringAfter stirring for 3 hours
  4. customthe catalyst is removed by filtration (Teflon millipore) and the filtrate
  5. concentrationis concentrated at reduced pressure
  6. customto give 3.15 g

Quellen und Nachweise

ORD-Eintrag
ord-7ed0d1b9d377446eab25b71c6cdd91d2
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04500518

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