Potassium Hydroxide → HCID 76684542, compound

HRID 925236Notes

Reaction equation

C(OC([N:6]1[CH2:22][CH2:21][C:10]2[C:11]3[CH:12]([CH2:19][CH3:20])[CH2:13][CH2:14][O:15][C:16]=3[CH:17]=[CH:18][C:9]=2[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>CCO.Cl.O>[CH2:19]([CH:12]1[C:11]2[C:10]3[CH2:21][CH2:22][NH:6][CH2:7][CH2:8][C:9]=3[CH:18]=[CH:17][C:16]=2[O:15][CH2:14][CH2:13]1)[CH3:20]

Participants

Conditions

Temperature: 120 °C

Procedure

Into a sealed tube, the product from step (i) (95 mg, 0.313 mmol) dissolved in EtOH (2 ml) and water (500 μl) was added. To this stirred solution, KOH (275 mg, 4.9 mmol) was added. The reaction mixture was heated to 120° C. for 24 hours. The reaction mixture was allowed to cool to room temperature and was diluted with 2M HCl (15 ml) and water (15 ml). The aqueous mixture was washed with EtOAc (2×). The aqueous layer was then basified with 2M NaOH to pH 10 and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the title compound as a yellow oil (40 mg). 1H NMR (300 MHz, CDCl3) δ 6.86 (d, J=8.1 Hz, 1H); 6.57 (d, J=8.1 Hz, 1H); 4.22-4.17 (m, 1H); 4.12-4.03 (m, 1H); 3.00-2.84 (m, 8H); 2.83-2.72 (m, 1H); 2.06 (bs, 1H); 1.97-1.92 (m, 2H); 1.56-1.45 (m, 2H); 1.01 (t, J=6.0 Hz, 3H); MS: ESI (positive): 232 (M+H).

Workup

temperatureto cool to room temperature
washThe aqueous mixture was washed with EtOAc (2×)
extractionextracted with DCM (3×)
washThe combined DCM extracts were washed with brine
dry with materialdried over Na2SO4, and solvent
customevaporated in vacuo

Sources & evidence

ORD record: ord-4cf067c7dc704f77ba58aa9b548c8851
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284277B2

Reaction notes

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