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Diethyl Ether → 5-(4-fluorophenyl)-1-(2-((2S,4S)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide

HRID 360016
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HRID 360016 반응식
[NH2:1][CH2:2][CH2:3][C@H:4]1OC(C)(C)[O:7][C@@H:6]([CH2:12][C:13]([OH:15])=[O:14])[CH2:5]1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=O)[CH:24]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:25]([C:35](=O)[CH:36]([CH3:38])[CH3:37])[C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:27])=[CH:19][CH:18]=1.C(OCC)C.[Cl-].[NH4+]>CS(C)=O.O>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[N:1]([CH2:2][CH2:3][C@H:4]3[CH2:5][C@H:6]([OH:7])[CH2:12][C:13](=[O:14])[O:15]3)[C:35]([CH:36]([CH3:38])[CH3:37])=[C:25]([C:26]([NH:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:27])[C:24]=2[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:21][CH:22]=1
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참가 물질

7

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HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 99098724-(4-Fluorophenyl)-2-(2-methyl-1-oxopropyl)-4-oxo-3,N-diphenylbutanamideHCID 117906292-[(4R,6R)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic Acid

생성물 1

HCID 139236655-(4-fluorophenyl)-1-(2-((2S,4S)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide
수율 24.7%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
105 °C

실험 절차

A solution of 0.26 g (1.21 mmol) of (±)-cis-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid and 0.504 g (1.20 mmol) of (±)4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide mixture of [R-(R*,R*)], [R-(R*,S*)], [S-(R*,R*)] and [S-(R*,S*)] isomers in 5 mL of dimethyl sulfoxide is heated at 105° C. for 15 hours. The solution is cooled and poured into 100 mL of diethyl ether and 50 mL of saturated ammonium chloride in water. The layers are separated and the organic layer washed with water (2×50 mL--and 5% sodium hydroxide solution (2×100 mL) to extract the intermediate from unreacted diketone). The aqueous layer is acidified with dilute hydrochloric acid solution and extracted with 30 mL of ethyl acetate. A drop of concentrated hydrochloric acid is added to the ethyl acetate solution and allowed to stand 18 hours. The solution is concentrated in vacuo and the concentrate is redissolved in 30 mL of ethyl acetate and treated with one drop of concentrated hydrochloric acid. The solution is stirred two hours, concentrated in vacuo, and dissolved in 6 mL of toluene. Trans-(±)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide crystalizes and is isolated by filtration. A total of 0.16 g of trans-(±)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide is isolated in two crops.

후처리

  1. temperatureThe solution is cooled
  2. customThe layers are separated
  3. washthe organic layer washed with water (2×50 mL
  4. extraction5% sodium hydroxide solution (2×100 mL) to extract the intermediate from unreacted diketone)
  5. extractionextracted with 30 mL of ethyl acetate
  6. additionA drop of concentrated hydrochloric acid is added to the ethyl acetate solution
  7. concentrationThe solution is concentrated in vacuo
  8. dissolutionthe concentrate is redissolved in 30 mL of ethyl acetate
  9. additiontreated with one drop of concentrated hydrochloric acid
  10. concentrationconcentrated in vacuo
  11. dissolutiondissolved in 6 mL of toluene
  12. customTrans-(±)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide crystalizes
  13. customis isolated by filtration

출처 및 근거

ORD 기록
ord-573fe5ddc096496082b30ef8f6df30a6
출처 데이터셋
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05003080

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