Sodium hydride → HCID 20780487, compound

HRID 351081Notes

Reaction equation

HRID 351081 reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[H-].[Na+].O=[CH:15][C:16]#[C:17][C:18]1[CH:19]=[C:20]([S:24]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1>O1CCCC1>[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[CH:15]/[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([S:24](=[O:26])(=[O:25])[NH:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 22492464HCID 22492464, compound

Product 1

HCID 20780487HCID 20780487, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trimethyl phosphonoacetate (0.81 g, 4.5 mmol) in dry tetrahydrofuran (20 ml) under an argon atmosphere at 15–20° C. sodium hydride (0.12 g, 5.0 mmol) was added. The mixture was stirred at ambient temperature for 1 hour, and a solution of 3-(3-oxoprop-1-ynyl)-N-phenylbenzenesulfonamide (54a) (0.44 g, 1.5 mmol) in dry tetrahydrofuran (20 ml) was added dropwise at 15–20° C. The reaction mixture was stirred at ambient temperature for 1 hour and quenched by 3% HCl (20 ml). The product was extracted with ethyl acetate (50 ml), the extract was washed with 5% NaHCO3, water and dried (Na2SO4). The solvents were removed under reduced pressure and the residue was chromatographed on silica gel with ethyl acetate-hexane (1:2, v/v) as eluent to give the title compound (0.39 g, 74%) as a white solid. M.p. 134–136° C. 1H NMR (DMSO-d6, HMDSO) δ: 3.73 (3H, s, CH3); 6.49 (1H, d, J=15.5 Hz, CH); 7.03 (1H, d, J=15.5 Hz, CH); 7.01–7.38 (5H, m, C6H5); 7.41–7.89 (4H, m, C6H4); 10.34 (1H, s, NH).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  2. customquenched by 3% HCl (20 ml)
  3. extractionThe product was extracted with ethyl acetate (50 ml)
  4. washthe extract was washed with 5% NaHCO3, water
  5. dry with materialdried (Na2SO4)
  6. customThe solvents were removed under reduced pressure
  7. customthe residue was chromatographed on silica gel with ethyl acetate-hexane (1:2

Sources & evidence

ORD record
ord-23e5d4c8316d4b7fae8a6af9de1e5833
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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