Sodium hydride → 4-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-6-yloxy)-butyric acid ethyl ester

HRID 1069582ノート

反応式

HRID 1069582 の反応式
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:19][C:20]([NH2:22])=[O:21])=[C:7]([CH3:18])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(Cl)Cl.CO.CCCCCC>O>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][O:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:19][C:20]([NH2:22])=[O:21])=[C:7]([CH3:18])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1)[CH3:33]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 105657326-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamideHCID 21959077Hexane methylene chloride methanol

生成物 1

HCID 105735094-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-6-yloxy)-butyric acid ethyl ester収率 76%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 294 mg (1 mmol) of 6-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide was treated with 40 mg (1 mmol) of 60% NaH/mineral oil and after 1 hours, 0.15 mL (1 mmol) of ethyl 4-bromobutyrate was added. The mixture was stirred for 2 hours, diluted with water and extracted with EtOAc. The EtOAc solution was washed with NaCl solution, dried (MgSO4), and concentrated at reduced pressure. The residue was chromatographed on silica eluting with EtOAc to give (after crystallizing from CH2Cl2/MeOH/hexane, 228 mg (76% yield) of 4-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-6-yl]oxy]butanoic acid ethyl ester, mp, 126-133° C.

後処理

  1. extractionextracted with EtOAc
  2. washThe EtOAc solution was washed with NaCl solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was chromatographed on silica eluting with EtOAc
  6. customto give (

出典と根拠

ORDレコード
ord-b0822de911be4d3e926d6fc04d5bdc5f
出典データセット
uspto-grants-2001_06
特許番号
US06252084B1

反応ノート

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