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

HRID 1664232노트

반응식

HRID 1664232 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3262b5a95bf04b1faf4b1dd1a2e5f99a
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039455B2

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