Hydrochloric Acid → {4-[(2-Phenylethyl)carbamoyl]phenyl}boronic acid

HRID 432271Notes

Reaction equation

HRID 432271 reaction equation
C([Li])C[CH2:3][CH3:4].[C:6]1([NH:12][C:13](=[O:23])[C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][C:15]=2OC)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[B:24](OC(C)C)([O:29]C(C)C)[O:25]C(C)C.Cl>O1CCCC1>[CH2:6]([NH:12][C:13]([C:14]1[CH:15]=[CH:16][C:17]([B:24]([OH:29])[OH:25])=[CH:18][CH:19]=1)=[O:23])[CH2:11][C:10]1[CH:9]=[CH:8][CH:7]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 223472094-Bromo-2-methoxy-N-phenylbenzamideHCID 178418339Butyllithium

Product 1

HCID 22346976{4-[(2-Phenylethyl)carbamoyl]phenyl}boronic acidYield 28.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium(1.6 M in hexane solution, 10 ml, 15.78 mmol) was added slowly to a solution of N1-phenyl-4-bromo-2-methoxybenzamide (1.92 g, 6.31 mmol) in tetrahydrofuran (47 mL) at −78° C. After 30 minutes, triisopropyl borate (2.2 mL, 9.47 mmol) was added rapidly. The reaction mixture was allowed to warm up to room temperature after 13 minutes and stirred for 16 hours. Hydrochloric acid (2.5N, 47 mL) was added and the mixture was stirred for 5 h hours. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was recrystallized from ethyl acetate/heptane to give 4-[(phenethylamino)carbonyl]phenylboronic acid (0.486 g, 28%). 1H NMR (DMSO-d6) δ 2.85 (m, 2H), 3.49 (m, 2H), 7.22 (m, 5H), 7.73 (m, 4H), 8.17 (s, 2H), 8.54 (m, 1H).

Workup

  1. stirringthe mixture was stirred for 5 h hours
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-dc8fd6e641b24bc9a150a45f9a49abc1
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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