Water → HCID 69199373, compound

HRID 851907Notes

Reaction equation

HRID 851907 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]=[S:8]1(=[O:33])[C:13]2[CH:14]=[C:15]([O:18][C:19]3[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=3)[C:22]([N:24]([CH3:26])[CH3:25])=O)[CH:16]=[CH:17][C:12]=2[N:11]2[CH2:30][CH2:31][CH2:32][C:10]2=[N:9]1.[H-].O>C1COCC1>[O:33]=[S:8]1(=[O:7])[C:13]2[CH:14]=[C:15]([O:18][C:19]3[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=3)[CH2:22][N:24]([CH3:26])[CH3:25])[CH:16]=[CH:17][C:12]=2[N:11]2[CH2:30][CH2:31][CH2:32][CH:10]2[NH:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 69523007HCID 69523007, compound

Product 1

HCID 69199373HCID 69199373, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.72 ml (3.72 mmol) of a 1M solution of LiAlH4 in THF are added dropwise to a suspension of 577 mg (1.49 mmol) of the product obtained in Step D in 20 ml of THF. The reaction mixture is observed passing into solution and stirring is carried out at ambient temperature for 3 hours. The excess of hydride is hydrolysed by the dropwise addition of water until the evolution of gas ceases. The suspension is stirred for 10 minutes, 20 ml of water are added, and extraction is carried out with AcOEt. The organic phases are combined, washed (saturated NaCl), dried (MgSO4) and evaporated, and the residue is chromatographed on a silica column (CH2Cl2/MeOH 95/5) to yield the title product.

Workup

  1. stirringThe suspension is stirred for 10 minutes
  2. extractionextraction
  3. washwashed (saturated NaCl)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customthe residue is chromatographed on a silica column (CH2Cl2/MeOH 95/5)

Sources & evidence

ORD record
ord-8bf0929257b44677b508ba427d6f3d66
Source dataset
uspto-grants-2007_08
Patent number
US07253162B2

Reaction notes

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