Water → t-Butyl 2-(benzyloxycarbonyl)amino-3-aminopropionate

HRID 263843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263843
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][NH2:17])[C:13]([O-:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][C:19](=[CH2:21])[CH3:20].O>O1CCOCC1.S(=O)(=O)(O)O>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][NH2:17])[C:13]([O:15][C:19]([CH3:21])([CH3:20])[CH3:18])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 8255IsobutyleneHCID 228745582-(S)-(benzyloxycarbonyl)amino-3-aminopropionate

Produkt 1

HCID 21584644t-Butyl 2-(benzyloxycarbonyl)amino-3-aminopropionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 2-(S)-(benzyloxycarbonyl)amino-3-aminopropionate (Fluka) (5.25 g, 22 mmol) in dioxane (75 mL) and conc. sulfuric acid (9 mL) was cooled to 0° C. and treated with 100 mL isobutylene in a Fisher Porter high pressure apparatus. The reaction was allowed to warm to room temperature and was stirred for 24 h. The reaction was vented, then poured into water (200 mL) to give an acidic solution that was extracted with ether (2×50 mL). The aqueous layer was carefully basified with conc. NaOH to pH 11-12 and extracted with 3×150 mL EtOAc. The EtOAc was removed in vacuo and the residue was azeotroped with toluene and dried under vacuum to give 4-1 as an oil. Rf (5% MeOH/CHCl3 saturated with NH3) 0.31. 1H NMR (400 MHz, CDCl3) δ7.3 (m, 5H), 5.6 (bs, 1H), 5.1 (s, 2H), 4.22 (bs, 1H), 3.05 (m, 2H), 1.45 (s, 9H), 1.4-1.2 (b, 2H).

Aufarbeitung

  1. customto give an acidic solution that
  2. extractionwas extracted with ether (2×50 mL)
  3. extractionextracted with 3×150 mL EtOAc
  4. customThe EtOAc was removed in vacuo
  5. customthe residue was azeotroped with toluene
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2f3b32a77b72485f94605419819b7ed3
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646000

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