Trimethyl borate → 3-(3-Heptyl-1-methylureido)phenylboronic acid

HRID 250930

Reaction equation

HRID 250930 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]([CH3:19])[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10])[CH:5]=[CH:6][CH:7]=1.C[Li].C([Li])(C)(C)C.[B:27](OC)([O:30]C)[O:28]C>O1CCCC1.CCCCC>[CH2:12]([NH:11][C:9](=[O:10])[N:8]([C:4]1[CH:3]=[C:2]([B:27]([OH:30])[OH:28])[CH:7]=[CH:6][CH:5]=1)[CH3:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 8470Trimethyl borateHCID 116168371-(3-Bromophenyl)-3-heptyl-1-methylureaHCID 178418306HCID 178418306, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 115583693-(3-Heptyl-1-methylureido)phenylboronic acidYield 36%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to that of Example (18a), by reaction of 113 g (0.345 mol, 1 eq) of 1-(3-bromophenyl)-3-heptyl-1-methylurea in 1.13 L of tetrahydrofuran, 127 mL (0.38 mol, 1.1 eq) of methyllithium, 530 mL (0.76 mol, 2.2 eq) of a 1.7M solution of tert-butyllithium in pentane and 97 mL (0.904 mol, 2.2 eq) of trimethyl borate, and after purification by chromatography on silica gel (50/50 heptane/ethyl acetate) and crystallization from ethyl acetate/heptane, 36.0 g of 3-(3-heptyl-1-methylureido)phenylboronic acid are obtained in the form of a pinkish powder. Yield=36%

Workup

  1. customafter purification by chromatography
  2. customon silica gel (50/50 heptane/ethyl acetate) and crystallization from ethyl acetate/heptane, 36.0 g of 3-(3-heptyl-1-methylureido)phenylboronic acid
  3. customare obtained in the form of a pinkish powder

Sources & evidence

ORD record
ord-a4d70830b5e943f6adba87c891408446
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Linked notes

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