(3-Acetamidophenyl)boronic acid → (+,-) Cis Propane-2-sulfonic Acid [2-(3'-acetamido-biphenyl-4-yl)-cyclopentyl]-amide

HRID 989514Notes

Reaction equation

HRID 989514 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.[C:20]([NH:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)(=[O:22])[CH3:21]>>[C:20]([NH:23][C:24]1[CH:29]=[C:28]([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:27]=[CH:26][CH:25]=1)(=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 157274(3-Acetamidophenyl)boronic acidHCID 10000637(R,R) Propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Product 1

HCID 59103250(+,-) Cis Propane-2-sulfonic Acid [2-(3'-acetamido-biphenyl-4-yl)-cyclopentyl]-amideYield 42%

Procedure

The Suzuki coupling of (+,−) Cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (200 mg, 0.51 mmol, prepared in example 17) and 3-acetamidophenylboronic acid (109 mg, 0.61 mmol) was accomplished in a manner analogous to the procedure described in example 27. The reaction was worked up in a manner analogous to example 3. Purification by silica chromatography using a Chromatotron® was achieved eluting with 2% methanol/methylene chloride to afford 85 mg (42%) of the title compound as a white solid when concentrated from ether.

Workup

  1. customPurification by silica chromatography
  2. washwas achieved eluting with 2% methanol/methylene chloride

Sources & evidence

ORD record
ord-ff8551345027468f90e872291563a0c8
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

Loading…