Hydrochloric Acid → HCID 20592594, compound

HRID 1369256Notes

Reaction equation

[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]3[CH2:26][C@@H:25]([CH2:27][C:28]([O:30]CC)=[O:29])[C:24]4[CH:33]=[CH:34][CH:35]=[CH:36][C:23]=4[CH2:22][C:21]=3[CH:37]=2)[CH:7]=1)[CH3:4].Cl>C(O)C>[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]3[CH2:26][C@@H:25]([CH2:27][C:28]([OH:30])=[O:29])[C:24]4[CH:33]=[CH:34][CH:35]=[CH:36][C:23]=4[CH2:22][C:21]=3[CH:37]=2)[CH:7]=1)[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

1.0 N NaOH (2.0 mL, 2.0 mmole) was added to a solution of ethyl (S)-10,11-dihydro-3-[3-(4-ethoxypyridin-2-ylamino)-1-propyloxy]-5H-dibenzo[a,d]cycloheptene-10-acetate (475.2 mg, 1.0 mmol) in absolute ethanol (10 mL), and the solution was warmed at 50° C. in an oil bath. After 20 hr, the reaction was concentrated and the aqueous residue was cooled to 0° C. in an ice bath. 1.0 N aqueous HCl (2.0 mL, 2.0 mmole) was slowly added with stirring. An opaque solid residue precipitated and was collected on a sintered glass funnel. Drying in a vacuum desiccator overnight gave the title compound (452.6 mg, 83%): MS (ES) m/e 447 (M+H)+. Anal. Calcd for C27H30N2O4.0.20 H2O.1.75 HCl: C, 63.10; H, 6.30; N, 5.45. Found: C, 63.10; H, 5.98; N, 5.38.

Workup

concentrationthe reaction was concentrated
temperaturethe aqueous residue was cooled to 0° C. in an ice bath
customAn opaque solid residue precipitated
customwas collected on a sintered glass funnel
customDrying in a vacuum desiccator overnight

Sources & evidence

ORD record: ord-4c4fba5e60f2427eb81f93daf0f59a7a
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06576643B2

Reaction notes

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