Tert-Butylamine → 5-(2,2-Dimethyl-propyl)-isoxazole-3-carboxylic acid tert-butylamide

HRID 1664232ノート

反応式

HRID 1664232 の反応式
[CH3:1][C:2]([CH3:13])([CH3:12])[CH2:3][C:4]1[O:8][N:7]=[C:6]([C:9]([OH:11])=O)[CH:5]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[C:35]([NH2:39])([CH3:38])([CH3:37])[CH3:36]>C1COCC1.CC#N>[C:35]([NH:39][C:9]([C:6]1[CH:5]=[C:4]([CH2:3][C:2]([CH3:1])([CH3:13])[CH3:12])[O:8][N:7]=1)=[O:11])([CH3:38])([CH3:37])[CH3:36]

参加物

7

反応物 4

HCID 6385Tert-ButylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 674399885-(2,2-Dimethyl-propyl)-isoxazole-3-carboxylic acid

生成物 1

HCID 674406745-(2,2-Dimethyl-propyl)-isoxazole-3-carboxylic acid tert-butylamide

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-(2,2-dimethyl-propyl)-isoxazole-3-carboxylic acid (125.4 g, 0.685 mol) in THF (1500 ml) and MeCN (1500 ml) is added HOBT (101.75 g, 0.753 mol) and EDCI (144.3 g, 0.753 mol). After stirred 30 min, tert-butyl amine (86.7 ml, 0.821 mol) is added dropwise under nitrogen atmosphere and then the reaction is stirred at rt for 1.5 h. The solvents are evaporated under reduced pressure and the residue is taken into DCM (2000 ml). The mixture is washed with saturated aq sodium bicarbonate (500 ml×2), the organic layer is dried over sodium sulfate and concentrated. The residue is purified by chromatography on silica (DCM) to give the product as white solid.

後処理

  1. stirringthe reaction is stirred at rt for 1.5 h
  2. customThe solvents are evaporated under reduced pressure
  3. washThe mixture is washed with saturated aq sodium bicarbonate (500 ml×2)
  4. dry with materialthe organic layer is dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography on silica (DCM)

出典と根拠

ORDレコード
ord-3262b5a95bf04b1faf4b1dd1a2e5f99a
出典データセット
uspto-grants-2011_10
特許番号
US08039455B2

反応ノート

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