Sodium Hydroxide → (R)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acid

HRID 84848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84848
[NH2:1][C@H:2]([CH2:6][CH:7]1[CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4].[OH-].[Na+].[C:12](=O)([O:18]C(C)(C)C)[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]>C(O)C.O.C1COCC1>[C:14]([O:13][C:12]([NH:1][C@H:2]([CH2:6][CH:7]1[CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4])=[O:18])([CH3:17])([CH3:16])[CH3:15]

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 9209421D-CyclopropylalanineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Produkt 1

HCID 2756015(R)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acidAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-amino-3-cyclopropylpropanoic acid (1.0 g, 7.7.4 mmol) in Ethanol (15 mL) and water (8 mL) was added 1N NaOH (10 mL) and Di-tert-butyl carbonate (1.86 g, 8.52 mmol) in THF (8 mL). After stirring at room temperature for 15 h, the solution was diluted with water, extracted with ether, the aqueous layer was separated and was acidified to pH 2 with conc. HCl, the aqueous layer was extracted with EtOAc, organic layer was separated, washed with brine, dried and concentrated to give (R)-2-(tert-butoxycarbonylamino)-3-cyclopropylpropanoic acid (1.0 g).

Aufarbeitung

  1. extractionextracted with ether
  2. customthe aqueous layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc, organic layer
  4. customwas separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-aea95d13432443cdb6388ff78383402d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846928B2

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