Sodium Hydroxide → tert-Butyl (2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoate

HRID 1109032

Reaktionsgleichung

Reaktionsgleichung von HRID 1109032
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[NH2:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].N([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[N+]=[N-].C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[Na+].[Na+].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.O.CCOCC>[C:32]([O:31][C:29]([NH:16][C@H:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:30])([CH3:35])([CH3:34])[CH3:33]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 7019766N5-benzyloxycarbonyl-ornithine, t-butyl esterHCID 21863217Citric acid sodium citrate

Produkt 1

HCID 10047875tert-Butyl (2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

Dissolve N5 -benzyloxycarbonyl-ornithine, t-butyl ester (3.22 g, 10 mmol) in 50/50 dioxane/water (25 mL) and buffer to pH 10 with 1N sodium hydroxide. Add, by dropwise addition, an ether solution of t-butyl azidoformate (1.58 g, 11 mmol) at 10° C. Allow to warm to room temperature and buffer occasionally to retain pH 10. Acidify with a sodium citrate/citric acid buffer to pH 5, extract with ether (3X) dry (MgSO4) and blow to a residue with a stream of nitrogen to give N-t-butyloxycarbonyl-N5 -benzyloxycarbonyl-ornithine, t-butyl ester.

Aufarbeitung

  1. additionAdd, by dropwise addition
  2. customat 10° C
  3. extractionextract with ether (3X)
  4. dry with materialdry (MgSO4) and blow to a residue with a stream of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-132960b0451248f2ae9144a272f06461
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05318992

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