4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → 4-(2-(3-(((Benzyloxycarbonyl)(methyl)amino)methyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acid

HRID 735655Notes

Reaction equation

HRID 735655 reaction equation
C(C1C=C(NC(=O)CCCC2C=CC([B:25]([OH:27])[OH:26])=CC=2)C=CC=1S(CC)(=O)=O)#N.[CH2:29]([O:36][C:37]([N:39]([CH2:41][C:42]1[CH:43]=[C:44]([NH:48][C:49]([O:51][CH2:52][CH2:53][C:54]2[CH:59]=[CH:58][C:57](Br)=[CH:56][C:55]=2[CH3:61])=[O:50])[CH:45]=[CH:46][CH:47]=1)[CH3:40])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:29]([O:36][C:37]([N:39]([CH2:41][C:42]1[CH:43]=[C:44]([NH:48][C:49]([O:51][CH2:52][CH2:53][C:54]2[CH:59]=[CH:58][C:57]([B:25]([OH:27])[OH:26])=[CH:56][C:55]=2[CH3:61])=[O:50])[CH:45]=[CH:46][CH:47]=1)[CH3:40])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acidHCID 578428744-(2-(3-(((Benzyloxycarbonyl)(methyl)amino)methyl)phenylcarbamoyloxy)ethyl)-3-methylphenylbromide

Product 1

HCID 578428984-(2-(3-(((Benzyloxycarbonyl)(methyl)amino)methyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acidYield 28%

Procedure

Using a procedure analogous to that used to prepare 6D, 60C (2.9 g, 5.6 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 60D (720 mg, 28%) as a solid. MS (ESI) m/z 475.3 (M−H)−.

Sources & evidence

ORD record
ord-7e779af1abe64f4387e91a649fe4bf0a
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…