P-Toluenesulfonamide → 3-Hydroxy-4-oxo-4-(toluene-4-sulfonylamino)-but-2-enoic acid (4-fluoro-benzyl)-methoxy-amide

HRID 2181092

Reaction equation

HRID 2181092 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[O:11][CH3:12])=[O:9])[C:4](=[O:21])O1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.[H-].[Na+]>C1COCC1>[F:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:10]([O:11][CH3:12])[C:8](=[O:9])[CH:7]=[C:5]([OH:6])[C:4](=[O:21])[NH:32][S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=2)(=[O:30])=[O:31])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 24758Sodium hydrideHCID 730332332-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide

Product 1

HCID 761691613-Hydroxy-4-oxo-4-(toluene-4-sulfonylamino)-but-2-enoic acid (4-fluoro-benzyl)-methoxy-amideYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide (309 mg, 1 mmol) and toluene-4-sulfonamide (171 mg, 1 mmol) were dissolved in 2 mL of THF. To this was added 40 mg of NaH (60% dispersion in mineral oil) and the resulting mixture stirred overnight. The reaction was quenched with 1N HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and solvent removed to yield an oily solid. The product was triturated with MeOH to yield 80 mg solid (19% yield). HRMS (M−H) calcd for C19H18FN2O6S: 412.0870. Found: 421.0876. Anal calcd for C19H19FN2O6S: C, 54.02; H, 4.53; N, 6.63. Found: C, 54.07; H, 4.51; N, 6.51. 1H NMR (500 MHz, CDCl3) δ: 2.44 (s, 3), 3.64 (s, 3), 4.76 (s, 2), 6.45 (s, 1), 7.03 (m, 2), 7.25 (m, 2), 7.35 (d, 2, J=8), 8.00 (d, 2, J=8), 9.11 (s, 1). 13C NMR (125 MHz, CDCl3) δ: 21.68, 48.21, 63.07, 92.21, 115.67, 115.84, 128.70, 129.64, 130.18, 131.01, 135.14, 145.55, 158.85, 159.30, 161.60, 163.56, 170.87.

Workup

  1. customThe reaction was quenched with 1N HCl
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customsolvent removed
  6. customto yield an oily solid
  7. customThe product was triturated with MeOH

Sources & evidence

ORD record
ord-9f35f5599c3d46649226320ac30791a4
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Linked notes

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