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

HRID 1279782ノート

反応式

HRID 1279782 の反応式
[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

参加物

6

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 23378029HCID 23378029、化合物

生成物 2

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3c6ebd231ce946cb9deaaa1834fc940b
出典データセット
uspto-grants-2002_09
特許番号
US06448278B2

反応ノート

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