Triethylamine → HCID 86661962, compound

HRID 82877Notes

Reaction equation

HRID 82877 reaction equation
S([N:11]=[N+:12]=[N-])(C1C=CC(C)=CC=1)(=O)=O.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[N+:11](=[C:24]([C:23](=[O:30])[CH2:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:21][CH:20]=1)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N-:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 14959491Ethyl 4-(4-methoxyphenyl)-3-oxobutanoate

Product 1

HCID 86661962HCID 86661962, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Synthesis of B can be performed in analogy to the protocol in J. Org. Chem. 2001, 66, 2509-2511. At 0° C. a solution of sodium azide (2.287 g, 35.2 mmol) in a minimum amount of water was added to a solution of tosylchloride (6.71 g, 35.2 mmol) in acetone (40 ml). The reaction mixture was stirred at 0° C. for 2 h. Acetone was evaporated and the remaining aqueous residue was extracted three times with Et2O, dried over MgSO4, filtrated and evaporated to provide the tosyl azide as a clear oil. The freshly prepared tosyl azide was dissolved in DCM (40.0 ml), a mixture of commercially available ethyl 4-(4-methoxy-phenyl)-3-oxobutanoate (5.54 g, 23.45 mmol) and triethylamine (4.90 ml, 35.2 mmol) in DCM (dichloromethane) was added, and stirred at room temperature over night. The product as evaporated and purified by flash chromatography on 80 g SiO2 using 20% EtOAc in cyclohexane to obtain 4.03 g of the desired product (15.36 mM; yield: 65%).

Workup

  1. additionwas added
  2. customThe product as evaporated
  3. custompurified by flash chromatography on 80 g SiO2 using 20% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-54f2980e0dce46a3a3df042e670c0256
Source dataset
uspto-grants-2014_09
Patent number
US08846743B2

Reaction notes

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