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

HRID 2182925ノート

反応式

HRID 2182925 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]([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

参加物

6

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3fc3e344729444f38fb72be1c2c47168
出典データセット
uspto-grants-2005_05
特許番号
US06897306B2

反応ノート

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