Boronic Acid → 4-(4-(3-((tert-Butoxycarbonyl(methyl)amino)methyl)-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid

HRID 735532Notes

Reaction equation

HRID 735532 reaction equation
C(C1C=C(NC(=O)CCCC2C=CC([B:25]([OH:27])[OH:26])=CC=2)C=CC=1S(CC)(=O)=O)#N.Br[C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH2:38][C:39]([NH:41][C:42]2[CH:43]=[CH:44][C:45]([S:58]([CH2:61][CH3:62])(=[O:60])=[O:59])=[C:46]([CH:57]=2)[CH2:47][N:48]([CH3:56])[C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:40])=[CH:32][CH:31]=1.CC1(C)COB(B2OCC(C)(C)CO2)OC1.B(O)O>>[C:51]([O:50][C:49]([N:48]([CH2:47][C:46]1[CH:57]=[C:42]([NH:41][C:39](=[O:40])[CH2:38][CH2:37][CH2:36][C:33]2[CH:34]=[CH:35][C:30]([B:25]([OH:27])[OH:26])=[CH:31][CH:32]=2)[CH:43]=[CH:44][C:45]=1[S:58]([CH2:61][CH3:62])(=[O:60])=[O:59])[CH3:56])=[O:55])([CH3:54])([CH3:53])[CH3:52]

Participants

5

Reactant 4

HCID 61668Boronic AcidHCID 2734316Bis(neopentyl glycolato)diboronHCID 57842603tert-Butyl 5-(4-(4-bromophenyl)butanamido)-2-(ethylsulfonyl)benzyl(methyl)carbamateHCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid

Product 1

HCID 578429044-(4-(3-((tert-Butoxycarbonyl(methyl)amino)methyl)-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acidYield 76%

Procedure

Using a procedure analogous to that used to prepare 6D, 17C (0.428 g, 0.76 mmol) was coupled to 5,5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] (0.202 g, 0.894 mmol) and then hydrolyzed to the free boronic acid to give 17D (0.260 g, 76%) as a white solid. MS (ESI) m/z 519.0 (M+H)+.

Sources & evidence

ORD record
ord-921a6f623cc440e1994563bf7993ca44
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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