Methanol → 3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

HRID 20516

反応式

HRID 20516 の反応式
C[Si](I)(C)C.[OH:6][C:7]1[CH:8]=[C:9]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:28])[CH2:25][O:26]C)[CH:22]=1)[C:10]([NH:12][C:13]1[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=1)=[O:11].CO.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[OH:6][C:7]1[CH:8]=[C:9]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:28])[CH2:25][OH:26])[CH:22]=1)[C:10]([NH:12][C:13]1[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=1)=[O:11]

参加物

6

反応物 4

HCID 887MethanolHCID 61475Sodium Thiosulfate PentahydrateHCID 85247Trimethylsilyl iodideHCID 59127168(S)-3-hydroxy-5-(1-methoxypropan-2-yloxy)-N-(5-methylpyrazin-2-yl)benzamide

生成物 1

HCID 591271143-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide収率 65.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Trimethylsilyl iodide (6.06 mL, 42.75 mmol) was added to a solution of 3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide (2.71 g, 8.55 mmol) in dry acetonitrile (150 mL) and stirred for 24 h. Methanol (30 mL) was added to quench the reaction and stirred for 10 mins. 10% w/v Aqueous sodium thiosulfate pentahydrate (20 mL) was added to the mixture and the organic solvents removed in vacuo. The residue was brought to pH5 with 1M hydrochloric acid and ethyl acetate (80 mL) added. A yellow solid (1.4 g) was separated by filtration. The aqueous filtrate was reextracted into ethyl acetate (2×80 mL) and the combined organic layers dried (MgSO4), filtered and the solvents removed in vacuo. This residue was combined with the yellow solid obtained above and purified by column chromatography, eluting with 5% to 10% methanol in DCM, to give the title compound (1.70 g)

後処理

  1. customto quench
  2. customthe reaction
  3. stirringstirred for 10 mins
  4. additionwas added to the mixture
  5. customthe organic solvents removed in vacuo
  6. additionadded
  7. customA yellow solid (1.4 g) was separated by filtration
  8. dry with materialthe combined organic layers dried (MgSO4)
  9. filtrationfiltered
  10. customthe solvents removed in vacuo
  11. customobtained above and
  12. custompurified by column chromatography
  13. washeluting with 5% to 10% methanol in DCM

出典と根拠

ORDレコード
ord-a3d716bb74894df081ff97cc6d96156d
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

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