(1-{1-[4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester → (1-{1-[4-(2-Amino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester

HRID 446993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446993
[C:1]([O:5][C:6](=[O:56])[N:7]([CH:9]([C:11](=[O:55])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[N:25]([C:41](=[O:54])[CH2:42][NH:43]C(OCC3C=CC=CC=3)=O)[CH2:26][CH:27]([C:28](=[O:40])[NH:29][C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO.CCOC(C)=O>[C:1]([O:5][C:6](=[O:56])[N:7]([CH:9]([C:11](=[O:55])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[N:25]([C:41](=[O:54])[CH2:42][NH2:43])[CH2:26][CH:27]([C:28](=[O:40])[NH:29][C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:15])([CH3:17])[CH3:16])[CH3:10])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 1

HCID 67280489(1-{1-[4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester

Produkt 1

HCID 67280817(1-{1-[4-(2-Amino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl esterAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

A solution of 59 (430 mg, 0.56 mmol) in 1:1 MeOH/EtOAc (4 mL) was treated with Pd/C (5% wet, ca. 100 mg) and placed under H2 (35 psi) using a Parr apparatus. After 3 h, the reaction mixture was filtered through syringe filter disc (Acrodisc-PSF-0.45 μM) and rinsed with MeOH. The filtrate was concentrated to afford crude 60 (350 mg) which was concentrated twice from anhydrous toluene (50 mL) and then used without further purification. Mass spectrum, m/z [637.5] (M+H)+.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered through syringe
  2. filtrationfilter disc (Acrodisc-PSF-0.45 μM)
  3. washrinsed with MeOH
  4. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-44e4170b77fb4fd4af53621f3d72224d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481495B2

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