BOC-Ala-Gly-OBzl → (S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acid

HRID 1379601

Reaktionsgleichung

Reaktionsgleichung von HRID 1379601
[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5])[CH3:3]>C(O)C.[Pd]>[NH:1]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5])[CH3:3]

Komponenten

4

Edukt 1

HCID 10980600BOC-Ala-Gly-OBzl

Produkt 1

HCID 192414(S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

1 g (3 mmol) of Boc-Ala-Gly-OBzl (11) is dissolved in 50 ml of absolute ethanol (Aldrich) followed by addition of 100 mg of 10% Pd-C (Aldrich) in a 100 ml round bottom flask equipped with a stirring bar. The reaction mixture is stirred under hydrogen gas atmosphere using a balloon on the top of the round bottom flask. After 24 h, the reaction mixture is filtered to remove the Pd-C; the filtrate is evaporated to give Boc-Ala-Gly-OH (12). 1H-NMR (CDCl3): 1.33 (3H, d, J=7 Hz), 1.41 (9H, s), 3.97 (2H, d, J=5.6 Hz), 4.2 (1H, m), 6.18 (1H, br), 7.50 (1H, br). FABMS: 247 (M+1).

Aufarbeitung

  1. customequipped with a stirring bar
  2. filtrationthe reaction mixture is filtered
  3. customto remove the Pd-C
  4. customthe filtrate is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c9eb7cd185aa49bbb02989e3f612758f
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05672584

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