(+,-) Trans Propane-2-sulfonic Acid [2-(4-iodo-phenyl)-cyclopentyl]-amide → (+,-) Trans 2,2,2-Trifluoro-N-(2-{4'-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-yl}-ethyl)-acetamide

HRID 989495Notes

Reaction equation

HRID 989495 reaction equation
I[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.[F:20][C:21]([F:43])([F:42])[C:22]([NH:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][CH:28]=1)=[O:23]>>[F:20][C:21]([F:42])([F:43])[C:22]([NH:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]3[CH2:12][CH2:11][CH2:10][C@H:9]3[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=2)=[CH:29][CH:28]=1)=[O:23]

Participants

3

Reactant 2

HCID 11784171(+,-) Trans Propane-2-sulfonic Acid [2-(4-iodo-phenyl)-cyclopentyl]-amideHCID 180063462,2,2-Trifluoro-n-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-acetamide

Product 1

HCID 87698884(+,-) Trans 2,2,2-Trifluoro-N-(2-{4'-[2-(propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-yl}-ethyl)-acetamideYield 39.8%

Procedure

(+,−) Trans propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (100 mg, 0.25 mmol, prepared in example 2) and 2,2,2-Trifluoro-N-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-acetamide (105 mg, 0.31 mmol) were treated as described in example 6. The reaction was purified by radial chromatography eluting with 70:30 hexanes:ethyl acetate to afford 48 mg (39%) of the title compound as a white solid. The NMR was consistent with the assigned structure.

Workup

  1. customThe reaction was purified by radial chromatography
  2. washeluting with 70:30 hexanes

Sources & evidence

ORD record
ord-8606f9c3afd94e84b0a4c26b1d127d85
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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