4-Carboxyphenylboronic Acid → HCID 10178294, compound

HRID 989516Notes

Reaction equation

HRID 989516 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]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)([OH:22])=[O:21]>>[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:6]=[CH:7][C:2]([C:26]2[CH:27]=[CH:28][C:23]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=2)=[CH:3][CH:4]=1)(=[O:16])=[O:15])[CH3:19]

Participants

3

Reactant 2

HCID 3121834-Carboxyphenylboronic AcidHCID 10000637(R,R) Propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Product 1

HCID 10178294HCID 10178294, compoundYield 108.2%

Procedure

The Suzuki coupling of (+,−) Cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (245 mg, 0.62 mmol, prepared in example 17) and 4-carboxybenzeneboronic acid (114 mg, 0.69 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 4% methanol/methylene chloride to afford 260 mg of the title compound which was further purified by semiprep C18 reverse phase HPLC to give 96 mg (40%) of the title compound as a white solid.

Workup

  1. customPurification by silica chromatography
  2. washwas achieved eluting with 4% methanol/methylene chloride

Sources & evidence

ORD record
ord-e370ac39c6214888a8637b39cc1ce98e
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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