Triethylamine → HCID 86661962, compound

HRID 587872Notes

Reaction equation

HRID 587872 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-methoxyphenyl)-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-1630390af23c44ceb073939c9f1192f8
Source dataset
uspto-grants-2016_01
Patent number
US09227930B2

Reaction notes

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