1,1'-Carbonyldiimidazole → (3R)-6-Cyclohexyl-N-hydroxy-3-(3-isopropyl-1,2,4-oxadiazol-5-yl)hexanamide

HRID 1279779노트

반응식

HRID 1279779 반응식
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH:20]([CH3:22])[CH3:21])[N:16]=2)[CH2:11][C:12](O)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:36][OH:37]>O1CCCC1>[NH3:16].[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH:20]([CH3:22])[CH3:21])[N:16]=2)[CH2:11][C:12]([NH:36][OH:37])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 59909812(3R)-6-cyclohexyl-3-(3-isopropyl-1,2,4-oxadiazol-5-yl)hexanoic acid

생성물 2

HCID 222AmmoniaHCID 9945086(3R)-6-Cyclohexyl-N-hydroxy-3-(3-isopropyl-1,2,4-oxadiazol-5-yl)hexanamide수율 47.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (3R)-6-cyclohexyl-3-(3-isopropyl-1,2,4-oxadiazol-5-yl)hexanoic acid (Preparation 47) (175 mg, 0.57 mmol) in anhydrous tetrahydrofuran (10 ml) was treated with 1,1′-carbonyldiimidazole (93 mg, 0.57 mmol) and the mixture stirred at room temperature under a nitrogen atmosphere for 1 hour. Hydroxylamine hydrochloride (40 mg, 0.57 mmol) was then added and the mixture stirred for 18 hours. The mixture was filtered and the solvent was removed from the filtrate under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (95:5:0.5) to afford the title compound as an oil (44 mg).

후처리

  1. stirringthe mixture stirred for 18 hours
  2. filtrationThe mixture was filtered
  3. customthe solvent was removed from the filtrate under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-c7a1c472b9a846c1b805c98f0ac139da
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448278B2

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