Diisopropylethylamine → HCID 68945571, compound

HRID 1876926Notes

Reaction equation

HRID 1876926 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH:7]([NH2:16])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:27][C:28]1[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[C:29]=1[C:30](Cl)=[O:31].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:17])[CH:7]([NH:16][C:30](=[O:31])[C:29]1[C:33]([CH3:38])=[CH:34][C:35]([CH3:37])=[CH:36][C:28]=1[CH3:27])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([I:15])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 516892Sodium BicarbonateHCID 13993144HCID 13993144, compound

Product 1

HCID 68945571HCID 68945571, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.5 g (4.32 mmol) of (1) and 2.9 ml (17.3 mmol) of DIPEA were dissolved in 15 ml of DCM and cooled to 0° C. 1.73 g (9.51 mmol) of 2,4,6-trimethylbenzoyl chloride were added and the solution was stirred at room temperature for 3 h. The solution was poured into saturated NaHCO3 and the aqueous layer was extracted with ethyl acetate. The organic layer was extracted with saturated NaHCO3, brine and dried over Na2SO4. The solvent was removed at the evaporator. The product was purified by column chromatography on silica gel using ethyl acetate/hexane to give 1.83 g of (2).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. extractionThe organic layer was extracted with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed at the evaporator
  5. customThe product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-cbfaba687e63477ea243ece753ef70f2
Source dataset
uspto-grants-2012_11
Patent number
US08309735B2

Reaction notes

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