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

HRID 2181092

反応式

HRID 2181092 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f35f5599c3d46649226320ac30791a4
出典データセット
uspto-grants-2005_05
特許番号
US06890942B2

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