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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
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HRID 1678505 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-159565143b1d44b499e968bbcb059403
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08008303B2

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