Triethylamine → 1,1-Dimethyl-2-oxo-2-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amino}ethyl acetate

HRID 1852901Notes

Reaction equation

HRID 1852901 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=2)[NH2:12])[O:3]1.C(N(CC)CC)C.[C:24]([O:27][C:28]([CH3:33])([CH3:32])[C:29](Cl)=[O:30])(=[O:26])[CH3:25]>CN(C)C(=O)C.C(OCC)(=O)C>[C:24]([O:27][C:28]([CH3:33])([CH3:32])[C:29](=[O:30])[NH:12][C:11]1[CH:13]=[CH:14][CH:15]=[C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)[CH:10]=1)(=[O:26])[CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1234962-Acetoxyisobutyroyl chlorideHCID 27346553-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 711386561,1-Dimethyl-2-oxo-2-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amino}ethyl acetateYield 83%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (220 mg) and triethylamine (0.182 mL) in N,N-dimethylacetamide (1.5 mL) chilled to 0° C. was added 2-chloro-1,1-dimethyl-2-oxoethyl acetate (0.175 mL) dropwise. After being stirred at room temperature for 1 h, the reaction mixture was diluted with ethyl acetate and washed with 1 M citric acid aqueous solution 3 times then brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (10-100% ethyl acetate in hexanes) gave the product (290 mg, 83%).

Workup

  1. washwashed with 1 M citric acid aqueous solution 3 times
  2. dry with materialThe organics were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification by column chromatography (10-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-61f870087b164d40bbcff926108beb38
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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