Tetrahydrofuran → HCID 178440768、化合物

HRID 2242255ノート

反応式

HRID 2242255 の反応式
[CH2:1]([N:3](CC)CC)C.[CH2:8]1[CH2:12]OC[CH2:9]1.[CH2:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:35]=[CH:34][C:31](C=O)=[CH:30][CH:29]=3)[N:24]=2)=[CH:19][CH:18]=1)[CH:14]([CH3:16])[CH3:15].C(O[BH-]([O:45][C:46](=[O:48])[CH3:47])OC(=O)C)(=O)C.[Na+].[C:50](O)(=O)C.[CH2:54]1[CH2:58]OC[CH2:55]1>CO>[C:54]([O:45][C:46]([C@H:47]1[CH2:12][C@@H:8]([NH:3][CH2:1][C:31]2[CH:34]=[CH:35][C:28]([C:25]3[N:24]=[C:23]([C:20]4[CH:19]=[CH:18][C:17]([CH2:13][CH:14]([CH3:15])[CH3:16])=[CH:22][CH:21]=4)[O:27][N:26]=3)=[CH:29][CH:30]=2)[CH2:9]1)=[O:48])([CH3:55])([CH3:58])[CH3:50]

参加物

7

反応物 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 184469664-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-YL]benzaldehydeHCID 23444217Acetic acid tetrahydrofuran

生成物 1

HCID 178440768HCID 178440768、化合物収率 44%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 3-cis-amino-cylcobutanecarboxylic acid tert-butyl ester (3.78 g, 19.6 mmol), triethylamine (4.0 mL, 29.4 mmol) and THF (100 mL) was added to a solution of 4-[5-(4-isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-benzaldehyde (6.0 g, 19.6 mmol) in acetic acid/THF (1:10, 100 mL) and stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (8.06 g, 39.2 mmol) was added to the reaction mixture, stirred at room temperature for 12 hours, treated with methanol (50.0 mL) and concentrated in vacuo. The resulting residue was taken up in dichloromethane, washed sequentially with brine, saturated NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica, 1:9-1:1 EtOAc:hexanes) provided the title compound (4.0 g, 44% yield) as a solid.

後処理

  1. stirringstirred at room temperature for 12 hours
  2. concentrationconcentrated in vacuo
  3. washwashed sequentially with brine, saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (silica, 1:9-1:1 EtOAc:hexanes)

出典と根拠

ORDレコード
ord-6d136bed5041475caa5d756bb0b224bd
出典データセット
uspto-grants-2010_03
特許番号
US07671043B2

反応ノート

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