Chloroform → HCID 66941792, compound

HRID 1173979Notes

Reaction equation

HRID 1173979 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH2:19][CH2:20][C:21]#[N:22])[CH:13]=[CH:12]2)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C([CH:33]([CH:35]([C:37]([O-])=O)O)O)([O-])=O.[Na+].[K+].C(Cl)(Cl)Cl.[CH2:46]1[CH2:50]OC[CH2:47]1>>[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH2:19][CH2:20][CH2:21][N:22]([CH2:47][CH2:46][CH3:50])[CH2:33][CH2:35][CH3:37])[CH:13]=[CH:12]2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 6212ChloroformHCID 8028TetrahydrofuranHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 66941797HCID 66941797, compound

Product 1

HCID 66941792HCID 66941792, compound

Procedure

The compound (139.9 mg) obtained in Example 119-8 was dissolved in anhydrous THF (4.2 ml). Then, lithium aluminum hydride (68.3 mg) was added to the solution, followed by stirring at room temperature for 2 hours. The solution was added with an aqueous potassium sodium tartrate solution and stirred at room temperature. After completion of the reaction, extraction with chloroform was carried out. The organic layer was dried with magnesium sulfate and the solvent was then distilled off under reduced pressure. The residue was added with anhydrous methanol (4.1 ml), propionaldehyde (0.095 ml), trimethyl orthoformate (0.144 ml), and sodium cyanoborohydride (110.6 mg) and stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. Then, the residue was dissolved in chloroform and washed with water, followed by drying with magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (toluene/ethyl acetate), thereby obtaining the subject compound (62.6 mg) as a yellow solid.

Workup

  1. stirringstirred at room temperature
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. distillationthe solvent was then distilled off under reduced pressure
  4. additionThe residue was added with anhydrous methanol (4.1 ml), propionaldehyde (0.095 ml), trimethyl orthoformate (0.144 ml), and sodium cyanoborohydride (110.6 mg)
  5. stirringstirred at room temperature for 2 hours
  6. customAfter completion of the reaction
  7. distillationthe solvent was distilled off under reduced pressure
  8. dissolutionThen, the residue was dissolved in chloroform
  9. washwashed with water
  10. dry with materialby drying with magnesium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. customThe residue was purified through silica gel column chromatography (toluene/ethyl acetate)

Sources & evidence

ORD record
ord-49d405b3b6994ac29ed4a565367aad60
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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