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 1678002Notes

Reaction equation

HRID 1678002 reaction equation
[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]

Participants

4

Reactant 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

Product 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-triamineYield 90.2%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

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 nm ins. 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.

Workup

  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)

Sources & evidence

ORD record
ord-8c7f52e1514340a489cd5035d86cdae1
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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