Acetyl chloride → HCID 68817368, compound

HRID 736757Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=[C:26]([CH3:34])[CH:25]=3)=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].[C:35](Cl)(=[O:37])[CH3:36]>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[CH:11]([NH:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=[C:26]([CH3:34])[CH:25]=3)=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]([C:35](=[O:37])[CH3:36])[CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid ethyl ester (0.6 g, 1.24 mmol) in CH2Cl2 (10 mL) and TEA (0.378 mL, 2.73 mmol) at 0° C. was added acetyl chloride (0.1 mL, 1.36 mmol). The reaction was allowed to warm to 25° C. over 19 h. The reaction was then taken up in CH2Cl2 (50 mL) and washed with 1N HCl (5 mL) and water (5 mL). The organics were washed with saturated aqueous sodium chloride (30 mL), dried over MgSO4, filtered and concentrated. The residue was purified with Biotage Flash 40S chromatography, eluting with 1:1 ethyl acetate-hexanes, to provide 1-acetyl-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid ethyl ester as a white solid (0.6 g, 92%). MS: 526 (M+H)+.

Workup

washwashed with 1N HCl (5 mL) and water (5 mL)
washThe organics were washed with saturated aqueous sodium chloride (30 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified with Biotage Flash 40S chromatography
washeluting with 1:1 ethyl acetate-hexanes

Sources & evidence

ORD record: ord-c5155e53c6b643a1bd480285ff4d3d2e
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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