Potassium Carbonate → HCID 10098811, compound

HRID 919015Notes

Reaction equation

HRID 919015 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([NH:11][NH:12][C:13]([C:15]1[CH:33]=[CH:32][C:18]2[O:19][CH2:20][CH:21]([CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[O:22][C:17]=2[C:16]=1[CH3:34])=[O:14])([CH3:10])([CH3:9])[CH3:8].[CH3:35][C:36]1[CH:37]=[C:38]([CH:42]=[C:43]([CH3:45])[CH:44]=1)[C:39](Cl)=[O:40].CCOCC.CCCCCC>C(OCC)(=O)C>[C:7]([N:11]([C:39](=[O:40])[C:38]1[CH:42]=[C:43]([CH3:45])[CH:44]=[C:36]([CH3:35])[CH:37]=1)[NH:12][C:13]([C:15]1[CH:33]=[CH:32][C:18]2[O:19][CH2:20][CH:21]([CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[O:22][C:17]=2[C:16]=1[CH3:34])=[O:14])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 810883,5-Dimethylbenzoyl ChlorideHCID 21584099Diethylether hexaneHCID 68775834HCID 68775834, compound

Product 1

HCID 10098811HCID 10098811, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a round bottom flask equipped with magnetic stirring was added ethyl acetate (7 mL), 25 wt % aqueous potassium carbonate solution (2.03 g, 3.67 mmol), and 3-(tert-butyldimethylsilyloxymethyl)-5-methyl-2,3-dihydrobenzo[1,4]dioxine-6-carboxylic acid N′-tert-butyl hydrazide (0.50 g, 1.22 mmol). To this was added 3,5-dimethylbenzoyl chloride (0.31 g, 1.84 mmol). Stirring was continued for 18 hours. The reaction was diluted with ethyl acetate and the phases separated. The organic phase was washed once with water, once with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and evaporated. The residue was flash chromatographed on silica gel eluting with 20% ether/hexane, then 50% ether/hexane to give a white solid, 3,5-dimethylbenzoic acid N-tert-butyl-N′-[3-(tert-butyldimethylsilyloxymethyl)-5-methyl-2,3-dihydrobenzo[1,4]dioxine-6-carbonyl]-hydrazide, (0.50 g, 0.92 mmol) in 76% yield. 1H-NMR (300 MHz, CD3COCD3) δ (ppm): 0.10 (s, 6H), 0.90 (s, 9H), 1.59 (s, 9H), 1.89 (s, 3H), 2.25 (s, 6H), 3.92 (m, 2H), 4.05 (m, 1H), 4.22 (m, 1H), 4.34 (m, 1H), 6.33 (d, 1H), 6.56 (d, 1H), 7.02 (s, 1H), 7.13 (s, 2H), 9.49 (s, 1H); TLC: Rf=0.30 (1:1 ether/hexane).

Workup

  1. customTo a round bottom flask equipped
  2. stirringStirring
  3. customthe phases separated
  4. washThe organic phase was washed once with water, once with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customchromatographed on silica gel eluting with 20% ether/hexane

Sources & evidence

ORD record
ord-d4ec3150989d4b53b1f35cec1196d6b1
Source dataset
uspto-grants-2016_03
Patent number
US09272986B2

Reaction notes

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