Hydrochloric Acid → HCID 67230744, compound

HRID 1805359Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([O-:17])=[O:16])[C:6](=[O:21])[C@@:5]12[CH2:23][C:22]1([CH3:25])[CH3:24].Cl>O1CCCC1.[OH-].[Na+].O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=[O:16])[C:6](=[O:21])[C:5]12[CH2:23][C:22]1([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of (R) and (S)-3-((5′-fluoro-2,2-dimethyl-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)methyl)benzoate (850 mg, 2.4 mmol) in tetrahydrofuran (10 mL) and 30% sodium hydroxide in water (5 mL) was stirred at 25° C. for 16 hours. The mixture was neutralized with a 2 N aqueous hydrochloric acid solution, diluted with ethyl acetate (50 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% trifluoro-acetic acid in water) afforded the title compound as white solid (410 mg, 50%): LC/MS m/e calcd. for C20H15FNO3 (M+H)+: 340.37, observed: 340.2; LC/MS m/e calcd. for C20H18FNO3: 339, observed (M+H)+: 340.1 1H NMR (400 MHz, DMSO-d6) δppm 1.37 (s, 3 H) 1.48 (s, 3 H) 1.76 (d, J=4.29 Hz, 1 H) 1.88 (d, J=4.29 Hz, 1 H) 5.04 (dd, 2 H) 6.91-7.08 (m, 2 H) 7.17 (dd, J=9.35, 2.53 Hz, 1 H) 7.44-7.57 (m, 2 H) 7.80-7.93 (m, 2H) 12.99 (s, 1 H).

Workup

washwashed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customPurification by waters

Sources & evidence

ORD record: ord-e4afafb97778442e98210c1cc0b75cb4
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354443B2

Reaction notes

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