Sodium Hydroxide → (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)ethanol

HRID 931753Notes

Reaction equation

C([O:7][CH2:8][C@@H:9]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:10]1[C:11]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([CH2:21][N:22]([CH3:24])[CH3:23])[CH:14]=[CH:13]2)(=O)C(C)(C)C.[OH-].[Na+]>C1COCC1.CO.O>[C:33]([O:32][C@@H:9]([C:10]1[C:11]([C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([CH2:21][N:22]([CH3:23])[CH3:24])[CH:14]=[CH:13]2)[CH2:8][OH:7])([CH3:36])([CH3:34])[CH3:35]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)ethyl pivalate (5.6 mg, 0.011 mmol) in THF and methanol (1.5 mL/0.5 mL) was added 2 M NaOH solution (0.5 mL, excess) at 0° C. The mixture was stirred at 50° C. for 3 hours, diluted with water and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated in vacuo. The obtained residue was purified by prep-HPLC to provide the desired product (3.0 mg, 64%). LCMS-ESI+ (m/z): 427.3, 429.2 (M+H)+.

Workup

extractionthe resulting mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
customdried
concentrationconcentrated in vacuo
customThe obtained residue was purified by prep-HPLC

Sources & evidence

ORD record: ord-2285003fea70449da2be719611dee9dd
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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