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Acetic Acid → N(4)-[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)cyclopentyl]-5-chloropyridine-2,3,4-triamine

HRID 1397605
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HRID 1397605 반응식
[Si:1]([O:8][C@@H:9]1[C@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:12][C@@H:11]([NH:23][C:24]2[C:29]([Cl:30])=[CH:28][N:27]=[C:26]([NH2:31])[C:25]=2[N+:32]([O-])=O)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(O)(=O)C>[Zn]>[Si:1]([O:8][C@@H:9]1[C@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:12][C@@H:11]([NH:23][C:24]2[C:29]([Cl:30])=[CH:28][N:27]=[C:26]([NH2:31])[C:25]=2[NH2:32])[CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]
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참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 66797989N(4)-[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)-silyl]oxy}methyl)cyclopentyl]-5-chloro-3-nitropyridine-2,4-diamine

생성물 1

HCID 66797912N(4)-[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)cyclopentyl]-5-chloropyridine-2,3,4-triamine수율 90.2%

시약·촉매·용매 1

HCID 23994Zinc
촉매

실험 절차

N(4)-[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)-silyl]oxy}methyl)cyclopentyl]-5-chloro-3-nitropyridine-2,4-diamine (0.875 g, 0.00165 mol) and zinc (0.431 g, 0.00659 mol) was added to acetic acid (40.0 mL, 0.704 mol) with stirring for 10 mins. The mixture was stirred for 10 min and the solid was filtered off. The filtrate was concentrated, dissolved in EtOAc (50 mL) washed with water (2×10). To the organic phase was added 2 ml Et3N and the mixture was washed with 10 mL water. The organic layer was concentrated and purified by flash chromatography (30% EtOAc/hexanes) to afford the title compound (0.746 g, 90%) as a white solid.

후처리

  1. stirringThe mixture was stirred for 10 min
  2. filtrationthe solid was filtered off
  3. concentrationThe filtrate was concentrated
  4. dissolutiondissolved in EtOAc (50 mL)
  5. washwashed with water (2×10)
  6. additionTo the organic phase was added 2 ml Et3N
  7. washthe mixture was washed with 10 mL water
  8. concentrationThe organic layer was concentrated
  9. custompurified by flash chromatography (30% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-8583f890ad2445c29635f1b49907ccca
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901136B2

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