Hydroxyamine hydrochloride → HCID 178453866, Verbindung

HRID 1051047Notizen

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[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])#[N:2].Cl.[NH2:21][OH:22]>CCO>[OH:22][NH:21][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[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[NH:2]

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

Prepared using General Procedure 3. To (R)-tert-butyl 4-cyano-2,3-dihydro-1H-inden-1-ylcarbamate INT-8 (15.0 g, 58.2 mmol) in EtOH (100 mL) was added hydroxylamine hydrochloride (12.1 g, 174.2 mmol) and TEA (17.6 mL, 174.2 mmol) and the reaction mixture heated at 85° C. for 2 h. The solvents were removed and the resulting white solid was partitioned between water and DCM. The organic layers were dried over Na2SO4, concentrated, and recrystallized from isopropanol (50 mL) to afford 14.4 g (85%) of (R)-tert-butyl 4-(N-hydroxycarbamimidoyl)-2,3-dihydro-1H-inden-1-ylcarbamate INT-10 as white crystalline solid. LCMS-ESI (m/z) calculated for C15H21N3O3: 291.4. found 292.1 [M+H]+, tR=2.04 min. 1H NMR (400 MHz, DMSO) δ 9.53 (s, 1H), 7.38-7.32 (m, 1H), 7.32-7.12 (m, 3H), 5.68 (s, 2H), 4.97 (q, J=8.5, 1H), 3.07 (ddd, J=16.6, 8.7, 2.6, 1H), 2.86 (dt, J=16.8, 8.4, 1H), 2.30 (ddd, J=12.6, 7.6, 3.6, 1H), 1.75 (dq, J=12.3, 9.0, 1H), 1.44 (s, 9H).

Aufarbeitung

customPrepared
customThe solvents were removed
customthe resulting white solid was partitioned between water and DCM
dry with materialThe organic layers were dried over Na2SO4
concentrationconcentrated
customrecrystallized from isopropanol (50 mL)

Quellen und Nachweise

ORD-Eintrag: ord-fae0aeca7dba4be8a0520f42f07c82a1
Quelldatensatz: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09388147B2

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