1,1'-Carbonyldiimidazole → tert-butyl (3R)-6-cyclohexyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)hexanoate

HRID 1279844

반응식

HRID 1279844 반응식
[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O[NH:35][C:36](=[NH:38])[CH3:37]>ClCCl>[CH:15]1([CH2:14][CH2:13][CH2:12][C@@H:8]([C:9]2[O:11][N:38]=[C:36]([CH3:37])[N:35]=2)[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 9835906(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acidHCID 178465666HCID 178465666, 화합물

생성물 1

HCID 59909764tert-butyl (3R)-6-cyclohexyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)hexanoate수율 57.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid (Preparation 1) (596 mg, 2.00 mmol) in dichloromethane (8ml) was treated with 1,1′-carbonyldiimidazole (364 mg, 2.25 mol) and the solution was stirred at room temperature for 15 minutes. The N-hydroxyacetamidine (Chem.Ber.; 17; 1884; 2746) (148 mg, 2.00 mmol) was then added and the mixture was stirred for 1 hour. The solvent was removed under reduced pressure and the residue was heated neat under a nitrogen atmosphere for 90 minutes. The crude product was then purified by column chromatography on silica gel eluting with dichloromethane to afford the title compound (385 mg).

후처리

  1. stirringthe mixture was stirred for 1 hour
  2. customThe solvent was removed under reduced pressure
  3. temperaturethe residue was heated neat under a nitrogen atmosphere for 90 minutes
  4. customThe crude product was then purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-0fd2fe6cb17647cd977ad92b3b7c3250
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448278B2

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