benzyl N-[2-(4-bromophenyl)ethyl]-N-methylcarbamate → 4-(2-((Benzyloxycarbonyl)(methyl)amino)ethyl)phenylboronic acid

HRID 735570Notes

Reaction equation

HRID 735570 reaction equation
C(C1C=C(NC(=O)C[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([B:25]([OH:27])[OH:26])=[CH:21][CH:20]=2)C=CC=1S(CC)(=O)=O)#N.BrC1C=CC(C[CH2:35][N:36](C)[C:37](=[O:46])[O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=CC=1>>[CH2:39]([O:38][C:37]([N:36]([CH3:35])[CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([B:25]([OH:26])[OH:27])=[CH:23][CH:24]=1)=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

3

Reactant 2

HCID 57842600benzyl N-[2-(4-bromophenyl)ethyl]-N-methylcarbamateHCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid

Product 1

HCID 578425784-(2-((Benzyloxycarbonyl)(methyl)amino)ethyl)phenylboronic acidYield 74%

Procedure

Using a procedure analogous to that used to prepare 6D, 28C (1.14 g, 3.3 mmol) was 5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 28D (760 mg, 74%) as a white solid. MS (ESI) m/z 313.97 (M+H)+.

Sources & evidence

ORD record
ord-b266c22af8eb437196afff097a9865af
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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