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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Triphenylphosphine → 6-(2,2-Diphenyl-ethylamino)-9-((1R,4S)-4-hydroxy-cyclopent-2-enyl)-9H-purine-2-carboxylic acid methyl ester

HRID 2382428
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인쇄 미리보기

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HRID 2382428 반응식
[CH3:1][O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][NH:11]2)=[C:7]([NH:14][CH2:15][CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:6]=1)=[O:4].[H-].[Na+].CC([O:34][C@H:35]1[CH:39]=[CH:38][C@@H:37](O)[CH2:36]1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:38]2[CH2:39][C@H:35]([OH:34])[CH:36]=[CH:37]2)=[C:7]([NH:14][CH2:15][CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:6]=1)=[O:4]
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참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 24758Sodium hydrideHCID 10154103rac-(1R,4S)-4-hydroxycyclopent-2-en-1-yl acetateHCID 178418823HCID 178418823, 화합물

생성물 1

HCID 666305706-(2,2-Diphenyl-ethylamino)-9-((1R,4S)-4-hydroxy-cyclopent-2-enyl)-9H-purine-2-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매

반응 조건

온도
40 °C

실험 절차

To 6-(2,2-diphenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester (5 g 13.4 mmol) under an atmosphere of argon is added dry deoxygenated tetrahydrofuran (100 ml) and dry dimethyl sulfoxide (2 ml). Sodium hydride 95% (0.32 g, 13.4 mmol) is then added and the solution is stirred at 40° C. Separately to (1S,4R)-cis 4-Acetoxy-2-cyclopenten-1-ol (1.89 g. 13.4 mmol), triphenylphosphine (0.53 g, 2.0 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.69 g, 0.67 mmol) is added dry deoxygenated tetrahydrofuran (20 ml) and the mixture stirred at room temperature for 10 minutes. This solution is added to the anion solution via syringe and the resulting mixture is then stirred at 80° C. The reaction is shown to be complete by LCMS after 2 hours. The reaction mixture is allowed to cool, methanol is added and a solid is filtered. The filtrate is concentrated in vacuo and the title compound is obtained by precipitation from dichloromethane/hexane. 1H NMR (MeOD, 400 MHz); 8.15(s, 1H), 7.40-7.15(m, 10H), 6.20(m, 1H), 5.95(m, 1H), 5.50(m, 2H), 4.75(m, 2H), 4.55(m, 1H), 4.10(m 2H), 3.90(s, 2H), 3.80(s, 1H), 2.9(m, 1H), 1.75(m, 1H).

후처리

  1. customdry
  2. customdeoxygenated tetrahydrofuran (100 ml) and dry dimethyl sulfoxide (2 ml)
  3. customdry
  4. customdeoxygenated tetrahydrofuran (20 ml)
  5. stirringthe mixture stirred at room temperature for 10 minutes
  6. additionThis solution is added to the anion solution via syringe
  7. stirringthe resulting mixture is then stirred at 80° C
  8. temperatureto cool
  9. additionmethanol is added
  10. filtrationa solid is filtered
  11. concentrationThe filtrate is concentrated in vacuo

출처 및 근거

ORD 기록
ord-43b098afa28a4d99b10392051caaabaf
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08258141B2

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