Water → (+/-)-5-(2-Methyl-propane-2-sulfinylamino)-2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-pentanoic acid methyl ester

HRID 230271

反応式

HRID 230271 の反応式
[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:9]1[N:13]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[N:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[CH2:5][CH2:6][CH:7]=O.[CH3:27][C:28]([S:31]([NH2:33])=[O:32])([CH3:30])[CH3:29].O.[BH4-].[Na+]>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:9]1[N:13]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[N:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[CH2:5][CH2:6][CH2:7][NH:33][S:31]([C:28]([CH3:30])([CH3:29])[CH3:27])=[O:32]

参加物

7

反応物 4

HCID 962Water2 回HCID 3382465Tert-ButanesulfinamideHCID 4311764Sodium borohydrideHCID 587635832-(6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-5-oxo-pentanoic acid methyl ester

生成物 1

HCID 58763604(+/-)-5-(2-Methyl-propane-2-sulfinylamino)-2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-pentanoic acid methyl ester

試薬・触媒・溶媒 2

HCID 76524Titanium tetraethoxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a magnetically stirred solution of 2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-5-oxo-pentanoic acid methyl ester 44a (0.066 g, 0.189 mmol) in THF (2 mL) at room temperature under Ar atmosphere was added 2-methyl-propane-2-sulfinic acid amide (0.023 g, 0.189 mmol) and titanium ethoxide (20 wt % solution in ethanol, 2 mL). The reaction mixture was stirred overnight at room temperature. Water (40 mL) was added, and the aqueous phase was extracted with ethyl acetate (2×40 mL). The combined organic layers were washed with water, dried (MgSO4), and concentrated in vacuo. The reaction mixture was redissolved in MeOH (2 mL) and sodium borohydride (0.014 mg, 0.378 mmol) was added at room temperature. The reaction mixture was stirred for 1 h at room temperature, then water (40 mL) was added, and the aqueous phase was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water, dried (MgSO4), and concentrated in vacuo to provide crude product.

後処理

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×40 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe reaction mixture was redissolved in MeOH (2 mL)
  6. stirringThe reaction mixture was stirred for 1 h at room temperature
  7. extractionthe aqueous phase was extracted with ethyl acetate (2×100 mL)
  8. washThe combined organic layers were washed with water
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customto provide crude product

出典と根拠

ORDレコード
ord-1f0f7094ad0f49a39acdd7168a078d69
出典データセット
uspto-grants-2009_07
特許番号
US07566725B2

関連ノート

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