4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → 4-(2-(3-((Tert-butoxycarbonyl(methyl)amino)methyl)-4-(isopropylsulfonyl)phenylcarbamoyloxy)ethyl)-3-ethylphenylboronic acid

HRID 735618Notes

Reaction equation

HRID 735618 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][O:38][C:39](=[O:63])[NH:40][C:41]2[CH:46]=[CH:45][C:44]([S:47]([CH:50]([CH3:52])[CH3:51])(=[O:49])=[O:48])=[C:43]([CH2:53][N:54]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH3:55])[CH:42]=2)=[C:32]([CH2:64][CH3:65])[CH:31]=1>>[C:59]([O:58][C:56]([N:54]([CH2:53][C:43]1[CH:42]=[C:41]([NH:40][C:39]([O:38][CH2:37][CH2:36][C:33]2[CH:34]=[CH:35][C:30]([B:25]([OH:27])[OH:26])=[CH:31][C:32]=2[CH2:64][CH3:65])=[O:63])[CH:46]=[CH:45][C:44]=1[S:47]([CH:50]([CH3:52])[CH3:51])(=[O:49])=[O:48])[CH3:55])=[O:57])([CH3:62])([CH3:61])[CH3:60]

Participants

3

Reactant 2

HCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acidHCID 57842899[3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid 2-(4-bromo-2-ethyl-phenyl)-ethyl ester

Product 1

HCID 578426934-(2-(3-((Tert-butoxycarbonyl(methyl)amino)methyl)-4-(isopropylsulfonyl)phenylcarbamoyloxy)ethyl)-3-ethylphenylboronic acidYield 59%

Procedure

Using a procedure analogous to that used to prepare 6D, 43A (650 mg, 1.1 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 43B (362 mg, 59%) as a brown oil. MS (ESI) m/z 563.2 (M+H)+.

Sources & evidence

ORD record
ord-98b3f1dc0bd84e72a8c712f3d1b4d472
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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