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Ethanol → N-(4-benzyloxycarbonylaminophenyl)-4-methyl-3-oxo-2-[1-phenyl-2-(4-fluorophenyl)-2-oxoethyl]pentanamide

HRID 277566
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HRID 277566 반응식
[CH3:1][CH:2]([CH3:16])[C:3](=[O:15])[C:4](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5]([NH2:7])=[O:6].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.C([N:28]([CH2:31]C)[CH2:29][CH3:30])C.[OH2:33].[CH3:34][CH2:35][OH:36]>[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[CH2:35]([O:36][C:31]([NH:28][C:29]1[CH:30]=[CH:11][C:10]([NH:7][C:5](=[O:6])[CH:4]([CH:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:22]([C:21]2[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=2)=[O:23])[C:3](=[O:15])[CH:2]([CH3:16])[CH3:1])=[CH:9][CH:8]=1)=[O:33])[C:34]1[CH:5]=[CH:4][CH:3]=[CH:2][CH:1]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 702EthanolHCID 962WaterHCID 8471TriethylamineHCID 680234-FluorobenzaldehydeHCID 867578684-Methyl-3-oxo-2-(phenylmethylene)pentanamide

생성물 1

HCID 18314607N-(4-benzyloxycarbonylaminophenyl)-4-methyl-3-oxo-2-[1-phenyl-2-(4-fluorophenyl)-2-oxoethyl]pentanamide

시약·촉매·용매

1
HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide촉매

실험 절차

Step B—N-(4-benzyloxycarbonylamino)phenyl)-4-methyl-3-oxo-2-(phenylmethylene)pentanamide (10 mmol), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (3 mmol), 4-fluorobenzaldehyde (10 mmol) and triethylamine (10 mmol) are heated at reflux in EtOH (150 mL). The progress of the reaction is monitored by tlc. When the reaction is complete, the mixture is cooled and added to water. The aqueous solution is extracted with EtOAc, and the extract is dried and evaporated. The residue is chromatographed to afford the product N-(4-benzyloxycarbonylaminophenyl)-4-methyl-3-oxo-2-[1-phenyl-2-(4-fluorophenyl)-2-oxoethyl]pentanamide 7 (R=4-NHCbz).

후처리

  1. temperaturethe mixture is cooled
  2. extractionThe aqueous solution is extracted with EtOAc
  3. customthe extract is dried
  4. customevaporated
  5. customThe residue is chromatographed

출처 및 근거

ORD 기록
ord-b23dcddd3e8f4628bde981e77c4992c7
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06355810B1

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