1-Hydroxybenzotriazole → 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide

HRID 926365

Reaktionsgleichung

[CH2:1]1[C:6]2=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][N:5]2[CH2:4][CH2:3][O:2]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:35]1([C@H:41]([NH2:44])[CH2:42][CH3:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C)C=O.O>[C:35]1([C@H:41]([NH:44][C:10]([C:7]2[CH:8]=[CH:9][N:5]3[CH2:4][CH2:3][O:2][CH2:1][C:6]=23)=[O:12])[CH2:42][CH3:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid (comp. no. 8a) (5 g, 29.9 mmol) in dimethylformamide (50 ml) was added 1-hydroxybenzotriazole (4.45 g, 32.9 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.31 g, 32.9 mmol). The mixture was stirred for 1 h at 50° C., then (R)-1-phenyl-propylamine (4.45 g, 32.9 mmol) was added and the mixture was stirred at 25° C. overnight. An excess of water was added, the precipitate was filtered off, washed with a small amount of water and dried in vacuo to give 5.05 g (59%) of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide as a white solid. LC/MS (method 2): Rt=1.05 min; m/z=285.23 (M+H+).

Aufarbeitung

stirringthe mixture was stirred at 25° C. overnight
filtrationthe precipitate was filtered off
washwashed with a small amount of water
customdried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-5f5e2214fbdb43c8b9d98ebdb3f8635f
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09284333B2

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