Water → 1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid

HRID 2378942ノート

反応式

HRID 2378942 の反応式
C([O:3][C:4]([C:6]1[NH:7][C:8](=[O:24])[N:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[CH:10]=1)=[O:5])C.O.O.[OH-].[Li+]>O1CCCC1>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([N:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[NH:7][C:8]2=[O:24])[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

参加物

5

反応物 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59006357Tert-butyl 4-(4-(ethoxycarbonyl)-2-oxo-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylate

生成物 1

HCID 590063701-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

tert-Butyl 4-(4-(ethoxycarbonyl)-2-oxo-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylate (400 mg, 1.179 mmol) was dissolved in tetrahydrofuran (10 mL). Water (10 mL) was added to the mixture followed by lithium hydroxide hydrate (180 mg, 4.29 mmol). Mixture was warmed to 70° C. and held with stirring for 16 hours. Mixture was cooled to room temperature. Reaction was quenched with 4.5 mL 1N hydrochloric acid. Material was extracted twice with ethyl acetate. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as white solid in 98% yield. MS (M−H)−=310.2.

後処理

  1. temperatureMixture was cooled to room temperature
  2. customReaction
  3. customwas quenched with 4.5 mL 1N hydrochloric acid
  4. extractionMaterial was extracted twice with ethyl acetate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-6afcdabe66f04c4fb6b1f90fa8964acd
出典データセット
uspto-grants-2008_12
特許番号
US07470680B2

反応ノート

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