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Citric Acid → 4-Hydroxy-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-4-(2-thienyl)butanamide

HRID 1851551
ノート
印刷プレビュー

反応式

HRID 1851551 の反応式
[O:1]=[C:2]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)[CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][C:14]([C:17]1[S:18][CH:19]=[CH:20][N:21]=1)=[CH:13]2)=[O:6].O1CCCC1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[OH:1][CH:2]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)[CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][C:14]([C:17]1[S:18][CH:19]=[CH:20][N:21]=1)=[CH:13]2)=[O:6]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 579017094-Oxo-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-4-(2-thienyl)butanamide

生成物 1

HCID 579016334-Hydroxy-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-4-(2-thienyl)butanamide収率 84.2%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

To a mixture of 4-oxo-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-4-(2-thienyl)butanamide (1.43 g), tetrahydrofuran (10 ml) and methanol (10 ml) was added sodium borohydride (0.16 g) at 0° C., and the mixture was stirred at the same temperature for 1 hr. To the reaction mixture was added 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (1.21 g, yield 84%) was obtained as colorless crystals from a fraction eluted with ethyl acetate. melting point 155-157° C.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-5dacf5a69ffc48f1abad29883ec9e663
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08957070B2

反応ノート

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