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

HRID 890233

反応式

HRID 890233 の反応式
[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]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 516875Potassium Permanganate2 回HCID 22250555N-BOC-(3,5-dimethyladamantan-1-yl)-glycine

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 23719240Potassium hydroxide monohydrate溶媒

反応条件

温度
90 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-048587230b6b4becab8d8bc15da7682b
出典データセット
uspto-grants-2006_02
特許番号
US06995183B2

関連ノート

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