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Hydrochloric Acid → HCID 14503313、化合物

HRID 442647
ノート
印刷プレビュー

反応式

HRID 442647 の反応式
C(OC([NH:11][C@@H:12]([CH:20]([CH3:22])[CH3:21])C(OC(=O)C)C#N)=O)C1C=CC=CC=1.Cl.C1([O:30]C)C=CC=CC=1.[O:32]1[CH2:37][CH2:36][O:35]CC1>>[NH2:11][C@@H:12]([CH:20]([CH3:22])[CH3:21])[CH:36]([OH:35])[C:37]([OH:32])=[O:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 312751,4-DioxaneHCID 228716173-(S)-[(benzyloxycarbonyl)amino]-2-acetoxy-4-methylpentanenitrile

生成物 1

HCID 14503313HCID 14503313、化合物収率 75%

実験手順

To a solution containing 3-(S)-[(benzyloxycarbonyl)amino]-2-acetoxy-4-methylpentanenitrile (see example 1 of WO 96/16080) (15.2 g, 50.0 mmol) in 183 mL of dioxane was added 183 mL of concentrated hydrochloric acid and 7.45 mL of anisole. The reaction mixture was heated to reflux overnight. The hydrolysis reaction was allowed to cool to room temperature and then concentrated in vacuo. The resulting aqueous solution was extracted with ether (2×). The aqueous phase was placed on a Dowex 50X8-100 column (H+ form, preeluted with deionized water to pH=7). The column was eluted with 2.0N ammonium hydroxide and the pure fractions concentrated to afford 5.53 g (75%) of 3-(S)-amino-2-(R,S)-hydroxy-4-methylpentanoic acid as a pale yellow solid. FAB MS [M+H] m/z; Calcd: 148, Found: 148.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customThe hydrolysis reaction
  4. concentrationconcentrated in vacuo
  5. extractionThe resulting aqueous solution was extracted with ether (2×)
  6. washThe column was eluted with 2.0N ammonium hydroxide
  7. concentrationthe pure fractions concentrated

出典と根拠

ORDレコード
ord-5067021c4e92440ca789805a09afaf3b
出典データセット
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05891852

反応ノート

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