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Tetrahydrofuran → 2-fluoro-5-[3-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]ureido]benzoic acid

HRID 1979378
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HRID 1979378 반응식
[C:1]1([CH3:44])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[N:14]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:13][CH:12]([NH:28][C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[C:34]([C:39]([O:41]C)=[O:40])[CH:33]=3)=[O:30])[C:11]2=[O:43])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.O.[OH-].[Li+].O1CCCC1>CO>[F:38][C:35]1[CH:36]=[CH:37][C:32]([NH:31][C:29]([NH:28][CH:12]2[C:11](=[O:43])[N:10]([CH2:9][C:7]([C:2]3[C:1]([CH3:44])=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:8])[C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[N:14]([C:22](=[O:27])[C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:13]2)=[O:30])=[CH:33][C:34]=1[C:39]([OH:41])=[O:40]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 212019031-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-fluorophenyl)urea

생성물 1

HCID 212019212-fluoro-5-[3-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]ureido]benzoic acid수율 64.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

1-[1-(2-Toluoylmethyl)-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-fluorophenyl)urea (510 mg) was dissolved in methanol (24 ml), aqueous lithium hydroxide monohydrate (178 mg) solution (12 ml) and tetrahydrofuran (12 ml) was added, and the mixture was refluxed for one hour. The reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid was added, and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and diisopropyl ether was added to the residue for trituration, collected by filtration, to thereby obtain 320 mg of the titled compound.

후처리

  1. temperaturethe mixture was refluxed for one hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid
  3. additionwas added
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure, and diisopropyl ether
  8. additionwas added to the residue for trituration
  9. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-8b9a1f330bb84098b8affbc4589d55bd
출처 데이터셋
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06239131B1

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