Hydrochloric Acid → 2-(4-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)-2,8-diazaspiro[4.5]decan-3-one

HRID 1920139ノート

反応式

HRID 1920139 の反応式
Cl.CN(C)S([N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH2:12][N:13]([CH2:26][C:27]1[CH:51]=[CH:50][C:30]([CH2:31][N:32]2[C:36](=[O:37])[CH2:35][C:34]3([CH2:42][CH2:41][N:40](C(OC(C)(C)C)=O)[CH2:39][CH2:38]3)[CH2:33]2)=[CH:29][CH:28]=1)[CH2:14][C:15]1[N:16](S(N(C)C)(=O)=O)[CH:17]=[CH:18][N:19]=1)(=O)=O.[OH-].[Na+]>>[NH:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH2:12][N:13]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:31][N:32]2[C:36](=[O:37])[CH2:35][C:34]3([CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)[CH2:33]2)=[CH:50][CH:51]=1)[CH2:14][C:15]1[NH:19][CH:18]=[CH:17][N:16]=1

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67502412tert-butyl 2-(4-{[bis({1-[(dimethylamino)sulfonyl]-1H-imidazol-2-yl}methyl)amino]methyl}benzyl)-3-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

生成物 1

HCID 675021312-(4-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)-2,8-diazaspiro[4.5]decan-3-one収率 99.6%

実験手順

A 2N-hydrochloric acid (5 mL) solution of the compound (480 mg) obtained in Example 45 was stirred at 80° C. for 3 hours. After the reaction solution was cooled to room temperature, the pH was adjusted to 12 with an aqueous 2N-sodium hydroxide solution. The aqueous layer was extracted four times with dichloromethane. The combined organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. After removing the anhydrous magnesium sulfate by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:10%-saturated aqueous ammonia-methanol=1:0→7:3) to obtain the title compound (277 mg) having the following physical properties.

後処理

  1. extractionThe aqueous layer was extracted four times with dichloromethane
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the anhydrous magnesium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate:10%-saturated aqueous ammonia-methanol=1:0→7:3)

出典と根拠

ORDレコード
ord-5a7b2badb7ac40918f59b166e5616096
出典データセット
uspto-grants-2012_05
特許番号
US08168783B2

反応ノート

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