1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-methoxy-N-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 573273Notes

Reaction equation

HRID 573273 reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[O:3]1.Cl.[CH3:20][NH:21][O:22][CH3:23].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH3:23][O:22][N:21]([CH3:20])[C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:1])([CH3:18])[O:3]2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Product 1

HCID 46739065N-methoxy-N-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideYield 64.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (10.05 g), N,O-dimethylhydroxylamine hydrochloride (4.35 g), WSC (9.32 g), HOBt (6.57 g), and TEA (6.21 ml) in DMF (80 ml) was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/AcOEt) and crystallized from hexane to give the title compound (7.60 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe extract was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/AcOEt)
  6. customcrystallized from hexane

Sources & evidence

ORD record
ord-fff0ea8ac59e4835b8ffe5c2e35c242a
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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