Hydrochloric Acid → HCID 76684634, compound

HRID 925249Notes

Reaction equation

C(OC([N:6]1[CH2:21][CH2:20][C:10]2[C:11]3[CH:12]([O:18][CH3:19])[CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=O)C.[OH-].[K+].O.Cl>C(O)C>[CH3:19][O:18][CH:12]1[C:11]2[C:10]3[CH2:20][CH2:21][NH:6][CH2:7][CH2:8][C:9]=3[CH:17]=[CH:16][C:15]=2[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 120 °C

Procedure

The product from step (b) (52 mg, 0.18 mmol) was dissolved in ethanol (2 and placed in a pressure tube. To this solution was added KOH (0.20 g, 3.60 mmol) and water (0.5 ml). The tube was sealed and the contents stirred at 120° C. for 48 hours. The reaction mixture was then cooled to RT and acidified with 2N HCl to pH 3. The aqueous mixture was then washed with diethyl ether (3×). The aqueous phase pH was then adjusted to 12 by addition of 2M NaOH and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried (Na2SO4), and solvent evaporated in vacuo to give the titled compound as a colorless oil (19 mg). 1H NMR (300 MHz, CDCl3) δ 7.02 (d, J=7.5 Hz, 1H); 6.98 (d, J=7.5 Hz, 1H); 4.92 (dd, J=5.4 Hz, 2.7 Hz, 1H); 3.35 (s, 3H); 3.15-2.76 (m, 10H); 2.24-2.12 (m, 2H); 1.99 (bs, 1H); MS: ESI (positive): 218 (M+1).

Workup

customplaced in a pressure tube
customThe tube was sealed
temperatureThe reaction mixture was then cooled to RT
washThe aqueous mixture was then washed with diethyl ether (3×)
additionThe aqueous phase pH was then adjusted to 12 by addition of 2M NaOH
extractionextracted with DCM (3×)
washThe combined DCM extracts were washed with brine
dry with materialdried (Na2SO4), and solvent
customevaporated in vacuo

Sources & evidence

ORD record: ord-21652a6b66124d2eb9b236343187ee27
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284277B2

Reaction notes

Loading…