Benzoyl chloride → HCID 67408824, compound

HRID 1949637Notes

Reaction equation

C[O:2][C:3]([N:5]1[CH2:9][CH:8]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH:7]2[N:20]([C:23](=[O:39])[CH:24]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:21][CH2:22][CH:6]12)=O.C(Cl)(=O)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C(Cl)Cl>[C:35]([O:34][C:32](=[O:33])[NH:31][CH:24]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[C:23]([N:20]1[CH2:21][CH2:22][CH:6]2[N:5]([C:3](=[O:2])[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:9][CH:8]([C:10]3[C:18]4[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=4)[NH:12][CH:11]=3)[CH:7]12)=[O:39])([CH3:36])([CH3:38])[CH3:37]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution containing amine 50 (258 mg, 0.5 mmol) in DCM (8 mL) was cooled to 0° C. TEA (73 mg, 0.72 mmol) was added followed by benzoyl chloride (85 mg, 0.61 mmol) and the reaction mixture was warmed to ambient temperature. After 20 min, the reaction mixture was diluted with DCM and the resulting organic solution was washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (hexanes/EtOAc, 1:1) to afford 278 mg (94%) of 55 as an off-white-colored foam. Mass spectrum, m/z [589.4] (M+H)+.

Workup

temperaturethe reaction mixture was warmed to ambient temperature
washthe resulting organic solution was washed successively with 1M HCl and brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash silica gel chromatography (hexanes/EtOAc, 1:1)

Sources & evidence

ORD record: ord-9836e17187a741b0a20ca9fd2c9d3414
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399683B2

Reaction notes

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