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Hydrochloric Acid → HCID 14503313, 화합물

HRID 430939
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HRID 430939 반응식
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]
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참가 물질

5

반응물 4

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

생성물 1

HCID 14503313HCID 14503313, 화합물수율 75%

실험 절차

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 2.0 N 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.

후처리

  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 2.0 N ammonium hydroxide
  7. concentrationthe pure fractions concentrated

출처 및 근거

ORD 기록
ord-824471da929840d39b1f0fd0c9fa08f5
출처 데이터셋
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06656910B2

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