Hydrochloric Acid → N-BOC-(3-hydroxy-5,7-dimethyladamant-1-yl)-glycine

HRID 890233

반응식

HRID 890233 반응식
[C:1]([N:8]([C:13]12[CH2:22][C:17]3([CH3:23])[CH2:18][CH:19]([CH2:21][C:15]([CH3:24])([CH2:16]3)[CH2:14]1)[CH2:20]2)[CH2:9][C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[O-:25][Mn](=O)(=O)=O.[K+].Cl>[OH-].[K+].O.CCOC(C)=O>[C:1]([N:8]([C:13]12[CH2:14][C:15]3([CH3:24])[CH2:16][C:17]([CH3:23])([CH2:18][C:19]([OH:25])([CH2:21]3)[CH2:20]1)[CH2:22]2)[CH2:9][C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 516875Potassium Permanganate2회HCID 22250555N-BOC-(3,5-dimethyladamantan-1-yl)-glycine

생성물 1

HCID 22250566N-BOC-(3-hydroxy-5,7-dimethyladamant-1-yl)-glycine수율 102%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 23719240Potassium hydroxide monohydrate용매

반응 조건

온도
90 °C

실험 절차

To a solution of N-BOC-(3,5-dimethyladamantan-1-yl)-glycine (1.79 g, 5.3 mmol) in 2% KOH/water (75 mL) at rt was added KMnO4 (1.0 g, 6.3 mmol). The reaction was heated to 90° C. for 2 h. An additional portion of KMnO4 (0.3 g, 1.9 mmol) was added and the reaction was heated at 90° C. for an additional 1.5 h. The reaction was then diluted with EtOAc (150 mL) and with vigorous mixing the pH was addjusted to ˜3 with 1N HCl. The EtOAc layer was separated and set aside. The aqueous layer was then extracted once more with EtOAc and twice with dichloromethane. The combined organics were dried over MgSO4, filtered and concentrated to give N-BOC-(3-hydroxy-5,7-dimethyladamant-1-yl)-glycine (1.91 g). MS m/e (M+H)+=354.2

후처리

  1. temperaturethe reaction was heated at 90° C. for an additional 1.5 h
  2. additionwith vigorous mixing the pH
  3. customThe EtOAc layer was separated
  4. extractionThe aqueous layer was then extracted once more with EtOAc and twice with dichloromethane
  5. dry with materialThe combined organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-048587230b6b4becab8d8bc15da7682b
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995183B2

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