Sodium Chlorite → HCID 86698768、化合物

HRID 1054778ノート

反応式

HRID 1054778 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:24]=[CH:23][C:16]2[O:17][C@H:18]([CH2:21][OH:22])[CH2:19][O:20][C:15]=2[CH:14]=1.Cl([O-])=[O:26].[Na+].P([O-])(O)(O)=O.[Na+]>CC(=CC)C.O.C(O)(C)(C)C.C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:26])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:24]=[CH:23][C:16]2[O:17][C@H:18]([CH2:21][OH:22])[CH2:19][O:20][C:15]=2[CH:14]=1

参加物

8

反応物 3

HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86698767HCID 86698767、化合物

生成物 1

HCID 86698768HCID 86698768、化合物収率 14.3%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 6386tert-Butanol溶媒HCID 105532-Methyl-2-butene溶媒

実験手順

A mixture of 6-chloro-5-[(2R)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1H-indole-3-carbaldehyde (1.0 g, 2.9 mmol), sodium chlorite (5.28 g, 58.3 mmol), sodium dihydrogen phosphate (9.06 g, 58.1 mmol) in 2-methyl-2-butene (10 mL), water (10 mL), t-butanol (10 mL) and acetonitrile (10 mL) was stirred overnight at room temperature. The mixture was quenched with saturated aqueous sodium bisulfite. Water (50 mL) and methylene chloride (50 mL) was added. The aqueous layer was extracted with methylene chloride (50 mL×3). The combined organic layer was dried over sodium sulfate, filtered and evaporated to give residue which was purified by reverse phase HPLC to give the title compound (105 mg, 14.3% yield).

後処理

  1. customThe mixture was quenched with saturated aqueous sodium bisulfite
  2. additionWater (50 mL) and methylene chloride (50 mL) was added
  3. extractionThe aqueous layer was extracted with methylene chloride (50 mL×3)
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give residue which
  8. customwas purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-e9022d7fa6af43c88f54b82b3b640700
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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