Sodium Hydroxide → 4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)-3-methylphenylboronic acid

HRID 735505Notes

Reaction equation

HRID 735505 reaction equation
B(C1C=CC(CCCC(O)=O)=CC=1)(O)O.[C:16]([C:18]1[CH:19]=[C:20]([NH:29][C:30](=[O:49])[CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([B:40]3[O:45]CC(C)(C)C[O:41]3)=[CH:36][C:35]=2[CH3:48])[CH:21]=[CH:22][C:23]=1[S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])#[N:17].[OH-].[Na+]>>[C:16]([C:18]1[CH:19]=[C:20]([NH:29][C:30](=[O:49])[CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([B:40]([OH:41])[OH:45])=[CH:36][C:35]=2[CH3:48])[CH:21]=[CH:22][C:23]=1[S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])#[N:17]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 578425984-(4-Boronophenyl)butanoic acidHCID 57842912N-(3-Cyano-4-(ethylsulfonyl)phenyl)-4-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-2-methylphenyl)butanamide

Product 1

HCID 578428924-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)-3-methylphenylboronic acidYield 62%

Procedure

Using a procedure analogous to that used to prepare 2B, 8C (212 mg, 0.44 mmol) was reacted with NaOH and then purified by silica gel chromatography (MeOH/DCM) to afford 8D (113 mg, 62%). 1H NMR (400 MHz, THF-d8) δ 1.21 (t, 3 H), 1.94-2.04 (m, 2 H), 2.40 (t, J=7.25 Hz, 2 H), 2.70 (t, J=7.47 Hz, 2 H), 3.31 (q, J=7.47 Hz, 2 H), 7.01 (s, 2 H), 7.08 (d, J=7.47 Hz, 1 H), 7.53 (d, J=7.47 Hz, 1 H), 7.56 (s, 1 H), 7.93 (dd, 1 H), 7.99 (d, 1 H), 1.00 (d, J=2.20 Hz, 1 H), 9.66 (s, 1 H).

Workup

  1. custompurified by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-0455e7e7482e46acac2545538f35b26f
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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