Triethylamine → HCID 11341579, Verbindung

HRID 1271496

Reaktionsgleichung

C(N(CC)CC)C.[NH2:8][C@@H:9]1[CH2:15][O:14][C@@H:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][N:11]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:10]1=[O:26].Cl[C:28](OC1C=CC([N+]([O-])=O)=CC=1)=[O:29].C(N(C(C)C)CC)(C)C.[Cl-].[O:50]=[C:51]1[N:57]([CH:58]2[CH2:63][CH2:62][NH2+:61][CH2:60][CH2:59]2)[CH2:56][CH2:55][C:54]2[CH:64]=[CH:65][CH:66]=[CH:67][C:53]=2[NH:52]1>O1CCCC1.ClCCl>[CH:23]1([CH2:22][N:11]2[C:10](=[O:26])[C@H:9]([NH:8][C:28]([N:61]3[CH2:62][CH2:63][CH:58]([N:57]4[CH2:56][CH2:55][C:54]5[CH:64]=[CH:65][CH:66]=[CH:67][C:53]=5[NH:52][C:51]4=[O:50])[CH2:59][CH2:60]3)=[O:29])[CH2:15][O:14][C@@H:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12]2)[CH2:25][CH2:24]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

Triethylamine (0.011 mL, 0.081 mmol) was added to a solution of (2S,6R)-6-amino-4-(cyclopropylmethyl)-2-phenyl-1,4-oxazepan-5-one (21 mg, 0.081 mmol) and 4-nitrophenyl chloroformate (16 mg, 0.081 mmol) in tetrahydrofuran (1 mL) at 0° C. After 30 min, diisopropylethylamine (0.042 mL, 0.242 mmol), 4-(2-oxo-1,2,4,5-tetrahydro-3H-1,3-benzodiazepin-3-yl)piperidinium chloride (23 mg, 0.081 mmol), and dichloromethane (1 mL) were added and the mixture heated to 50° C. After 1 h, the mixture was allowed to cool to ambient temperature and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (34 mg). MS 532 (M+1).

Aufarbeitung

waitAfter 1 h
temperatureto cool to ambient temperature
concentrationconcentrated
customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag: ord-25f891b1b86d4611bbc13b21676ab193
Quelldatensatz: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07205292B2

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