Acetic Acid → HCID 22644806, compound

HRID 1976407Notes

Reaction equation

HRID 1976407 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH2:24][C:25]#[CH:26])[CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].C=O.[C:29](O)(=O)[CH3:30].[CH2:33]([NH:35][CH2:36]C)[CH3:34]>O1CCOCC1>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]([CH2:24][C:25]#[C:26][CH2:36][N:35]([CH2:29][CH3:30])[CH2:33][CH3:34])[CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8021DiethylamineHCID 22644688HCID 22644688, compound

Product 1

HCID 22644806HCID 22644806, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1.00 g (2.653 mmol) of methyl 2-[{[4-(2-butynyloxy)phenyl]sulfonyl}(2-propynyl)amino]-3-methylbutanoate in 8.0 mL of dioxane was added 0.198 g (6.632 mmol) of paraformaldehyde, 10 mg of cuprous chloride, 1.0 mL of acetic acid and 0.55 ml (5.305 mmol) diethylamine. The resulting mixture was stirred at room temperature for 15 minutes after which the reaction had turned green. The reaction was then heated to reflux for 2 h, after which the reaction had turned brown- The reaction mixture was cooled to room temperature and extracted with ether. The combined organics were washed with saturated sodium bicarbonate solution, dried over Na2SO4, filtered and concentrated in vacuo to give 1.23 g of methyl 2-{{[4-(2-butynyloxy)phenyl]sulfonyl}[4-(diethylamino)-2-butynyl]amino}-3-methylbutanoate as a brown oil.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 2 h
  3. temperaturewas cooled to room temperature
  4. extractionextracted with ether
  5. washThe combined organics were washed with saturated sodium bicarbonate solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53ec3d86a775459f9f64d21491cb2436
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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