Tetrahydrofuran → HCID 66941927, compound

HRID 1174001Notes

Reaction equation

HRID 1174001 reaction equation
[C:1]([O:5][C:6](=[O:25])[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][CH2:22][C:23]#[N:24])[CH:13]=[CH:12]2)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C([CH:35]([CH:37]([C:39]([O-])=O)O)O)([O-])=O.[Na+].[K+].[CH2:44]1[CH2:48]OC[CH2:45]1>>[C:1]([O:5][C:6](=[O:25])[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][CH2:22][CH2:23][N:24]([CH2:45][CH2:44][CH3:48])[CH2:35][CH2:37][CH3:39])[CH:13]=[CH:12]2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 66941274HCID 66941274, compound

Product 1

HCID 66941927HCID 66941927, compound

Procedure

The compound (75.8 mg) obtained in Example 123-3 was dissolved in anhydrous THF (2.2 ml). Then, the solution was added with lithium aluminum hydride (33.4 mg) and stirred at room temperature for 1 hour. An aqueous potassium sodium tartrate solution was added in this solution, and the whole was stirred, followed by extraction with chloroform. The organic layer was dried with magnesium sulfate and the solvent was then dried off. The residue was dissolved in anhydrous methanol (2.3 ml) and added with propionaldehyde (0.048 ml), trimethyl orthoformate (0.072 ml), and sodium cyanoborohydride (55.3 mg), followed by stirring at room temperature for 19 hours. The solvent was distilled off. Subsequently, the solvent was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (56.6 mg) as a yellow solid.

Workup

  1. stirringthe whole was stirred
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. customthe solvent was then dried off
  5. dissolutionThe residue was dissolved in anhydrous methanol (2.3 ml)
  6. additionadded with propionaldehyde (0.048 ml), trimethyl orthoformate (0.072 ml), and sodium cyanoborohydride (55.3 mg)
  7. stirringby stirring at room temperature for 19 hours
  8. distillationThe solvent was distilled off
  9. customSubsequently, the solvent was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ce1ab695c928481ea777cdfa0feac3ec
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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