Acetic Anhydride → (3-(Acetamidomethyl)phenyl)boronic acid

HRID 2234838Notes

Reaction equation

HRID 2234838 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.Cl.[NH2:9][CH2:10][C:11]1[CH:12]=[C:13]([B:17]([OH:19])[OH:18])[CH:14]=[CH:15][CH:16]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:5]([NH:9][CH2:10][C:11]1[CH:12]=[C:13]([B:17]([OH:19])[OH:18])[CH:14]=[CH:15][CH:16]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 16427085Boronic acid, B-(3-(aminomethyl)phenyl)-, hydrochloride (1:1)

Product 1

HCID 22309455(3-(Acetamidomethyl)phenyl)boronic acidYield 23.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (76 μL, 0.80 mmol) was added dropwise to a stirred solution of (3-aminomethylphenyl)boronic acid, hydrochloride (150 mg, 0.80 mmol) and DIEA (560 μL, 3.2 mmol) in CH2Cl2 (5 mL) at 0° C. After 1 h, the solution was concentrated in vacuo and purified by preparatory HPLC to give 36 mg (23%) of the title compound as a white solid. [M+H] calc'd for C9H12BNO3, 194; found, 194.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. custompurified by preparatory HPLC

Sources & evidence

ORD record
ord-0ce74f2ae8ad4ffe89e9e0df7f504ac6
Source dataset
uspto-grants-2010_05
Patent number
US07713973B2

Reaction notes

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