4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → (R)-4-(2-(3-(1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acid

Participants

Role	Name	HCID	Charge
Reactant	4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid	HCID 57842684	—
Reactant	(R)-ethyl 3-(benzyloxycarbonylamino)-3-(3-((4-bromo-2-methylphenethoxy)carbonylamino)phenyl)propanoate	HCID 57842714	—
Product	(R)-4-(2-(3-(1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acid	HCID 57842846	64%

Reaction Steps

Using a procedure analogous to that used to prepare 6D, 39D (1.07 g, 1.84 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 39E (640 mg, 64%) as a tan foam. 1H NMR (400 MHz, CD3OD) δ ppm 1.14 (t, J=7.15 Hz, 3 H) 2.65-2.86 (m, 2 H) 2.99 (t, J=7.15 Hz, 2 H) 4.05 (q, J=7.15 Hz, 2 H) 4.19-4.35 (m, 2 H) 4.93-5.14 (m, 3 H) 6.98 (d, J=7.70 Hz, 1 H) 7.12-7.33 (m, 8 H) 7.34-7.45 (m, 2 H) 7.45-7.59 (m, 1 H) 9.14 (s, 1 H)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07592331B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-e702661202fd43758f9e0fea9064ddce
Source note	uspto-grants-2009_09