(2H-1,3-benzodioxol-5-yl)boronic acid → 2-{[3',4'-Methylenedioxy-(1,1'-biphenyl)-4-yl]-sulfonyl}-amino-5-phenylpent-4-ynoic acid

HRID 1531320Notes

Reaction equation

HRID 1531320 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([C:19]([NH2:33])([CH2:24][C:25]#[C:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:20]([O:22]C)=[O:21])(=[O:18])=[O:17])=[CH:12][CH:11]=3)=[CH:4][C:3]=2[O:2]1.C1OC2C(=CC=C(B(O)O)C=2)O1>>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([C:19]([NH2:33])([CH2:24][C:25]#[C:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:20]([OH:22])=[O:21])(=[O:18])=[O:17])=[CH:12][CH:11]=3)=[CH:4][C:3]=2[O:2]1

Participants

3

Reactant 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 70223167Methyl 2-{[3',4'-Methylenedioxy-(1,1'-biphenyl)-4-yl]-sulfonyl}-amino-5-phenylpent-4-ynoate

Product 1

HCID 701145712-{[3',4'-Methylenedioxy-(1,1'-biphenyl)-4-yl]-sulfonyl}-amino-5-phenylpent-4-ynoic acid

Procedure

Methyl 2-{[3′,4′-Methylenedioxy-(1,1′-biphenyl)-4-yl]-sulfonyl}-amino-5-phenylpent-4-ynoate: The starting sulfonamide 3a (804 mg, 1.72 mmol) and 4-methylenedioxyphenylboronic acid (430 mg, 2.59 mmol) are coupled to give the title compound as described for compound 3b. The crude product is adsorbed onto silica and eluted through flash silica with hexanes:EtOAc (2:1 to 1:3) to give a pale yellow solid.

Sources & evidence

ORD record
ord-027852dcb6734336912fe5495c4cfb8a
Source dataset
uspto-grants-2001_03
Patent number
US06197770B1

Reaction notes

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