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

Participants

Role	Name	HCID	Charge
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	4-(4-Boronophenyl)butanoic acid	HCID 57842598	—
Reactant	N-(3-Cyano-4-(ethylsulfonyl)phenyl)-4-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-2-methylphenyl)butanamide	HCID 57842912	—
Product	4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)-3-methylphenylboronic acid	HCID 57842892	62%

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07592331B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-0455e7e7482e46acac2545538f35b26f
Source note	uspto-grants-2009_09