Water → (S)-tert-Butyl (4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamate

HRID 1055358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1055358
[NH2:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7](O)=[O:8].Cl.CN(C)CCCN=C=NCC.O>CN(C=O)C>[O:8]=[C:7]1[C@@H:6]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5][O:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=2[NH:1]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18599735(S)-3-(2-aminophenoxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Produkt 1

HCID 18599719(S)-tert-Butyl (4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of (S)-3-(2-amino-phenoxy)-2-tert-butoxycarbonylamino-propionic acid (3.8 g, 12.8 mmol, 1 eq) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI, 2.46 g, 12.8 mmol, 1 eq) in DMF (56.4 mL) was stirred for 1 h 45 min. The reaction was poured into H2O (250 mL) and extracted with EtOAc. The combined extracts were washed with H2O, dried over Na2SO4 and concentrated to give the title compound (3.1 g, 87%) as a tan solid which was used without purification.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with H2O
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1ca5891b47564a4a959e881e9b03746c
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394263B2

Notizen zur Reaktion

Wird geladen…