Sulfuric Acid → (S)-a-Hydroxy-cyclopropanepropanoic acid

HRID 2185527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185527
OS(O)(=O)=O.N([O-])=[O:7].[Na+].N[C@@H:11]([CH2:15][CH:16]1[CH2:18][CH2:17]1)[C:12]([OH:14])=[O:13].[Na+].[Cl-]>O>[OH:7][C@@H:11]([CH2:15][CH:16]1[CH2:18][CH2:17]1)[C:12]([OH:14])=[O:13]

Komponenten

6

Edukt 4

HCID 1118Sulfuric Acid2×HCID 5234Sodium ChlorideHCID 6951383(2S)-2-amino-3-cyclopropylpropanoic acidHCID 23668193Sodium Nitrite2×

Produkt 1

HCID 21341065(S)-a-Hydroxy-cyclopropanepropanoic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A 1 L, 3-neck flask was equipped with two dropping funnels, one containing 21.3 mL of 2.0 N H2SO4 and the other containing 21.3 mL of 2.0 N NaNO2. A mixture of 5.00 g (38.7 mmol) of 2-(S)-amino-3-cyclopropyl propanoic acid in 28 mL of H2O at 0° C. was treated with a sufficient amount of the acid solution to dissolve the solids. The remaining H2SO4 solution and the NaNO2 solution were added maintaing the internal temperature at less than 5° C. The resulting mixture was stirred cold for 3 h, then warmed to rt and stirred for 20 h. The reaction mixture was saturated with NaCl and extracted with 4×100 mL of EtOAc. The extracts were dried over MgSO4 and concentrated to afford 4.30 g (85%) of the title compound: 1H NMR (300 MHz): δ0.13-0.18 (m, 2H), 0.48-0.54 (m, 2H), 0.89 (m, 1H), 1.67‥1.76 (m, 2H), 4.37 (dd, J=6.4, 4.7 Hz, 1H).

Aufarbeitung

  1. additionwas treated with a sufficient amount of the acid solution
  2. dissolutionto dissolve the solids
  3. customat less than 5° C
  4. stirringstirred for 20 h
  5. extractionextracted with 4×100 mL of EtOAc
  6. dry with materialThe extracts were dried over MgSO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ff73a329cc5e46a4afb0ef6b3875f572
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399619B1

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