Ammonia → (S)-tert-butyl 1-amino-3-cyclopropyl-1-oxopropan-2-ylcarbamate

HRID 624885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624885
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[N:32]1C=CC=CC=1.N>C(#N)C>[NH2:32][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH:14]1[CH2:16][CH2:15]1

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 5706350(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acid

Produkt 1

HCID 70082562(S)-tert-butyl 1-amino-3-cyclopropyl-1-oxopropan-2-ylcarbamateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of (S)-2-(tert-butoxycarbonylamino)-3-cyclopropylpropanoic acid (CAN 89483-06-7, 10 g, 44 mmol), di-tert-butyl dicarbonate (CAN:24424-99-5, 14.28 g, 66 mmol) and pyridine (2.4 mL) in acetonitrile (200 mL) was stirred at room temperature for 20 min. Ammonia (10 mL) was added dropwise for 20 min. The resulting reaction mixture was stirred for 4 h. During removal of most of the solvent under reduced pressure the product precipitated and the solid was filtered off and washed with acetonitrile (20 mL). The solid was dried under reduced pressure to give the title compound (7.73 g, 78%) as white solid; MS (EI): m/e 251.2 [M+Na]+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 4 h
  3. customDuring removal of most of the solvent under reduced pressure the product
  4. customprecipitated
  5. filtrationthe solid was filtered off
  6. washwashed with acetonitrile (20 mL)
  7. customThe solid was dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3d6210924cbb44549b69d168bacf4b68
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303012B2

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