1,1'-Carbonyldiimidazole → (3R)-6-Cyclohexyl-N-hydroxy-3-{3-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2,4-oxadiazol-5-yl}hexanamide

HRID 1279782노트

반응식

HRID 1279782 반응식
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH2:20][C:21](=[O:27])[N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[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.[NH2:41][OH:42]>O1CCCC1>[NH3:16].[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH2:20][C:21](=[O:27])[N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[N:16]=2)[CH2:11][C:12]([NH:41][OH:42])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 23378029HCID 23378029, 화합물

생성물 2

HCID 222AmmoniaHCID 10178627(3R)-6-Cyclohexyl-N-hydroxy-3-{3-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1,2,4-oxadiazol-5-yl}hexanamide수율 48.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (3R)-6-cyclohexyl-3-{3-[2-oxo-2-(1 -pyrrolidinyl)ethyl]-1,2,4-oxadiazol-5-yl}hexanoic acid (Preparation 53) (200 mg, 0.53 mmol) in anhydrous tetrahydrofuran (10 ml) was treated with 1,1′-carbonyldiimidazole (86 mg, 0.53 mmol) and the mixture stirred at room temperature under a nitrogen atmosphere for 2 hours. Hydroxylamine hydrochloride (37 mg, 0.53 mmol) was then added and the mixture stirred for 18 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (90:10:1) to afford the title compound as a colourless oil (50 mg).

후처리

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

출처 및 근거

ORD 기록
ord-3c6ebd231ce946cb9deaaa1834fc940b
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448278B2

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