6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one → 6-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propylamino]-4H-benzo[1,4]oxazin-3-one

HRID 1259834

Reaktionsgleichung

Reaktionsgleichung von HRID 1259834
[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][CH2:7][C@@H:8]1[CH2:10][O:9]1)([CH3:4])([CH3:3])[CH3:2].[NH2:13][C:14]1[CH:15]=[CH:16][C:17]2[O:22][CH2:21][C:20](=[O:23])[NH:19][C:18]=2[CH:24]=1>CC#N>[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][CH2:7][C@@H:8]([OH:9])[CH2:10][NH:13][C:14]1[CH:15]=[CH:16][C:17]2[O:22][CH2:21][C:20](=[O:23])[NH:19][C:18]=2[CH:24]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 27636816-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 10954307(S)-Glycidoxy-t-butyldimethylsilane

Produkt 1

HCID 667376956-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propylamino]-4H-benzo[1,4]oxazin-3-oneAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of tert-butyl-dimethyl-((S)-1-oxiranylmethoxy)-silane (commercial; 13.0 g, 69 mmol) in MeCN (220 mL) was added LiClO4 (22 g, 207 mmol). 6-amino-4H-benzo[1,4]oxazin-3-one (commercial; 11.45 g, 64 mmol) was added and the mixture was stirred at 50° C. for 6 h. The solvent was removed in vacuo and the residue was purified by CC (DCM/MeOH/NH4OH 1000/25/2 to 1000/100/2) to afford the title intermediate as a pale brown foam (11.16 g, 44% yield).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by CC (DCM/MeOH/NH4OH 1000/25/2 to 1000/100/2)

Quellen und Nachweise

ORD-Eintrag
ord-9ed9890e33ac4d40be18c75db3f7c8bd
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466168B2

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