Benzoyl chloride → (+,-) Cis N-{4-[2-(Propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide

HRID 989501Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:18][CH:17]([S:14]([NH:13][C@H:9]1[CH2:10][CH2:11][CH2:12][C@H:8]1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][CH:6]=1)(=[O:16])=[O:15])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

(+,−) Cis propane-2-sulfonic acid [2-(4-amino-phenyl)-cyclopentyl]-amide (265 mg, 0.94 mmol, prepared in example 23) was dissolved in 10 mL of methylene chloride and cooled to 0° C. under nitrogen. Benzoyl chloride was added (120 uL, 1.03 mmol) and after stirring 15 min the ice bath was removed and stirring continued for 2 hours. The reaction was diluted with methylene chloride and washed with water, then 0.1 N HCl and dried over sodium sulfate. The organic phase was concentrated in vacuo to 360 mg crude oil. The product was purified by radial chromatography eluting first with 70:30 methylene chloride:hexanes then ethyl acetate was added (→20%) until all bands were removed to give 120 mg (33%) of the title compound as a white solid. The NMR was consistent with the assigned structure.

Workup

customwas removed
additionThe reaction was diluted with methylene chloride
washwashed with water
dry with material0.1 N HCl and dried over sodium sulfate
concentrationThe organic phase was concentrated in vacuo to 360 mg crude oil
customThe product was purified by radial chromatography
washeluting first with 70:30 methylene chloride
additionhexanes then ethyl acetate was added (→20%) until all bands
customwere removed

Sources & evidence

ORD record: ord-94f8fd78886a43c5aa1d89af3baa434c
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06639107B1

Reaction notes

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