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Hydrochloric Acid → (S)-2-{4'-[4-(4-Methanesulfonyl-piperazin-1-ylmethyl)-phenylcarbamoyl]-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl}-azetidine-1-carboxylic acid

HRID 1678505
ノート
印刷プレビュー

反応式

HRID 1678505 の反応式
C([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[C:12](=[O:51])[NH:13][C:14]1[CH:15]=[C:16]([C:25]2[CH:30]=[CH:29][C:28]([C:31](=[O:50])[NH:32][C:33]3[CH:38]=[CH:37][C:36]([CH2:39][N:40]4[CH2:45][CH2:44][N:43]([S:46]([CH3:49])(=[O:48])=[O:47])[CH2:42][CH2:41]4)=[CH:35][CH:34]=3)=[CH:27][CH:26]=2)[C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:18][CH:19]=1)=[O:7])(C)(C)C.Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:49][S:46]([N:43]1[CH2:44][CH2:45][N:40]([CH2:39][C:36]2[CH:37]=[CH:38][C:33]([NH:32][C:31]([C:28]3[CH:27]=[CH:26][C:25]([C:16]4[C:17]([O:20][C:21]([F:22])([F:24])[F:23])=[CH:18][CH:19]=[C:14]([NH:13][C:12]([C@@H:9]5[CH2:10][CH2:11][N:8]5[C:6]([OH:7])=[O:5])=[O:51])[CH:15]=4)=[CH:30][CH:29]=3)=[O:50])=[CH:34][CH:35]=2)[CH2:41][CH2:42]1)(=[O:48])=[O:47]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67372397(S)-2-{4'-[4-(4-Methanesulfonyl-piperazin-1-ylmethyl)-phenylcarbamoyl]-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl}-azetidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 16222129(S)-2-{4'-[4-(4-Methanesulfonyl-piperazin-1-ylmethyl)-phenylcarbamoyl]-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl}-azetidine-1-carboxylic acid

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A mixture of (S)-2-{4′-[4-(4-Methanesulfonyl-piperazin-1-ylmethyl)-phenylcarbamoyl]-6-trifluoromethoxy-biphenyl-3-ylcarbamoyl}-azetidine-1-carboxylic acid tert-butyl ester in dioxan (5 ml) was treated with conc. hydrochloric acid (3 ml) and the mixture stirred at room temp for 18 h. The mixture was then carefully basified with solid potassium carbonate and the mixture then was extracted with DCM. The residue was then purified on silica gel. Elution initially with DCM:EtOH:ammonia; 200:8:1 gave a colourless foam (impure). Further purification eluting with DCM:MeOH:AcOH:water; 90:10:1:1 gave a colourless gum (nmr suggests probably acetate salt of desired product). This material was then dissolved in DCM:EtOH:ammonia;25:8:1 and then passed down an SCX cartridge giving the title compound as a colourless solid (14 mg). This material is still not entirely pure as shown by 1H NMR. No further purification of this material was carried out.

後処理

  1. extractionthe mixture then was extracted with DCM
  2. customThe residue was then purified on silica gel
  3. washElution initially with DCM
  4. custom200:8:1 gave a colourless foam (impure)
  5. customFurther purification
  6. washeluting with DCM
  7. custom90:10:1:1 gave a colourless gum (nmr

出典と根拠

ORDレコード
ord-159565143b1d44b499e968bbcb059403
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08008303B2

反応ノート

読み込み中…

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