Hydrochloric Acid → HCID 59536664、化合物

HRID 1922176ノート

反応式

HRID 1922176 の反応式
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]([O:18][C:19]2[C:20]([CH3:27])=[N:21][C:22]([NH:25][CH3:26])=[CH:23][CH:24]=2)[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:9]1)=O)(C)(C)C.Cl>>[CH3:27][C:20]1[C:19]([O:18][CH:13]([C@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:24][CH:23]=[C:22]([NH:25][CH3:26])[N:21]=1

参加物

3

反応物 2

HCID 313Hydrochloric AcidHCID 66737795HCID 66737795、化合物

生成物 1

HCID 59536664HCID 59536664、化合物収率 12%

実験手順

Stir a mixture of (3S)-3-[1-(2-methyl-6-methylamino-3-pyridyloxy)-3-methyl-butyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (S-2) and aqueous HCl (4M, 0.261 mL, 1.04 mmol) at room temperature for 1 hour. After full conversion, concentrate the mixture, dissolve in dichloromethane and load the mixture onto a pre-packed SCX column. Wash with dichloromethane followed by methanol. Release the product with 2M NH3 in methanol and concentrate under reduced pressure. Purify the crude residue by reverse phase chromatography (17-43% gradient actonitrile in 0.01 M ammoniumformate in water, 85 mL/min, for 8 min., C18 ODB XBridge column, 30×75 mm, 5 μm) to give 9 mg (12%) of (3S)-3-[1-(2-methyl-6-methylamino-3-pyridyloxy)-3-methyl-butyl]-pyrrolidine (S-2). MS (m/z)=278 [M+1].

後処理

  1. concentrationAfter full conversion, concentrate the mixture
  2. dissolutiondissolve in dichloromethane
  3. washWash with dichloromethane
  4. concentrationconcentrate under reduced pressure
  5. customPurify the crude residue by reverse phase chromatography (17-43% gradient actonitrile in 0.01 M ammoniumformate in water, 85 mL/min, for 8 min., C18 ODB XBridge column, 30×75 mm, 5 μm)

出典と根拠

ORDレコード
ord-6c61291de4464440a039ad67976ef330
出典データセット
uspto-grants-2012_05
特許番号
US08173821B2

反応ノート

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