Diisopropylcarbodiimide → Tert-butyl 4-(3-(3,4-dichlorophenyl)-1,2,4-oxadiazol-5-yl)butylcarbamate

HRID 880031노트

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HRID 880031 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1[Cl:27])/[C:20](=[N:22]/O)/[NH2:21].CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C.N1C=CC=CC=1.CCOC(C)=O>[Cl:16][C:17]1[CH:18]=[C:19]([C:20]2[N:22]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[O:15][N:21]=2)[CH:24]=[CH:25][C:26]=1[Cl:27]

참가 물질

8

반응물 3

HCID 12734DiisopropylcarbodiimideHCID 5458485-(((Tert-butoxy)carbonyl)amino)pentanoic acidHCID 112641853,4-Dichloro-N'-hydroxybenzene-1-carboximidamide

생성물 1

HCID 86730084Tert-butyl 4-(3-(3,4-dichlorophenyl)-1,2,4-oxadiazol-5-yl)butylcarbamate수율 30.5%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

The 5-(tert-butoxycarbonylamino)pentanoic acid (424 mg, 1.95 mmol) was introduced into a microwave vial charged with DMAP (238 mg, 1.95 mmol) and Intermediate 20A (400 mg, 1.95 mmol). The reactants were dissolved in DMF (5 mL) and the DIC (0.304 mL, 1.95 mmol) was added. The reaction mixture was stirred at rt overnight. The reaction mixture was diluted with 3 mL of pyridine. The vial was capped and the reaction was heated in the microwave at 145° C. for 20 min. The reaction mixture was allowed to cool to rt. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic portion was concentrated under reduced pressure and purified by silica gel chromatography with EtOAc/Hexane to give Intermediate 20B as a white solid (230 mg, 0.595 mmol, 30.5% yield). HPLC/MS (Method D) RT=2.40 min [M+H]+ 385.9.

후처리

  1. customThe vial was capped
  2. temperaturethe reaction was heated in the microwave at 145° C. for 20 min
  3. temperatureto cool to rt
  4. washwashed with water and brine
  5. concentrationThe organic portion was concentrated under reduced pressure
  6. custompurified by silica gel chromatography with EtOAc/Hexane

출처 및 근거

ORD 기록
ord-18d104a6a6314c1e8f010e3ebec57d20
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993557B2

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