Sodium Hydroxide → 4-(4-(4-(tert-Butylsulfonyl)-3-cyanophenylamino)-4-oxobutyl)phenylboronic acid

Participants

Role	Name	HCID	Charge
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	4-(4-Boronophenyl)butanoic acid	HCID 57842598	—
Reactant	N-(4-(tert-butylsulfonyl)-3-cyanophenyl)-4-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)butanamide	HCID 57842633	—
Product	4-(4-(4-(tert-Butylsulfonyl)-3-cyanophenylamino)-4-oxobutyl)phenylboronic acid	HCID 57842768	71%

Reaction Steps

Using a procedure analogous to that used to prepare 2B, 10D (431 mg, 0.869 mmol) was reacted with NaOH to give 10E (263 mg, 71%) as a brown solid. 1H NMR (400 MHz, THF-d8) δ 1.34 (s, 9 H), 1.96-2.07 (m, 2 H), 2.35 (t, J=7.25 Hz, 2 H), 2.69 (t, J=7.25 Hz, 2 H), 7.09 (s, 1 H), 7.16 (d, J=7.91 Hz, 2 H), 7.71 (d, J=8.35 Hz, 2 H), 7.92-7.96 (m, 1 H), 8.01 (dd, J=2.20 Hz, 1 H), 8.23 (d, J=2.20 Hz, 1 H), 9.69-9.77 (m, 1 H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07592331B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-99361ccf4b8d47eb91e45116e883a7f2
Source note	uspto-grants-2009_09