Triethylamine → HCID 178484623, Verbindung

HRID 1051063Notizen

Reaktionsgleichung

[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C@@H:7]2[N:12]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])#[N:2].Cl.[NH2:27][OH:28].C(N(CC)CC)C>CCO>[CH3:25][N:23]([CH3:24])[C:21](=[O:22])[CH2:20][N:12]([C@@H:7]1[C:8]2[C:4](=[C:3]([C:1](=[NH:2])[NH:27][OH:28])[CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

Prepared using General Procedure 3. To a solution of (S)-tert-butyl 4-cyano-2,3-dihydro-1H-inden-1-yl(2-(dimethylamino)-2-oxoethyl)carbamate (3.8 g, 11.07 mmol) in EtOH (20 mL) was added hydroxylamine hydrochloride (1.92 g, 27.67 mmol) and triethylamine (2.8 g, 27.67 mmol). The reaction solution was heated to 85° C. for 2 h. The solvent was removed under vacuum and the residue partitioned between DCM (3×10 mL) and water (10 mL). The combined organic layers were dried over MgSO4 and concentrated under vacuum to produce 4.10 g (87.7%) of (S)-tert-butyl 2-(dimethylamino)-2-oxoethyl(4-(N-hydroxycarbamimidoyl)-2,3-dihydro-1H-inden-1-yl)carbamate, which was 65% pure and used directly in the next experiment. LCMS-ESI (m/z) calculated for C19H28N4O4; 376.45. found 377.2 [M+H]+, tR=1.85 min.

Aufarbeitung

customPrepared
customThe solvent was removed under vacuum
customthe residue partitioned between DCM (3×10 mL) and water (10 mL)
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-17e54ca530674253b9ff40c3928648cf
Quelldatensatz: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09388147B2

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