Water → HCID 19348240, compound

HRID 1637287Notes

Reaction equation

HRID 1637287 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH:7]2[C:17]3[C:18]4[C:10](=[C:11]([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[NH:12][C:13]=4[CH:14]=[CH:15][CH:16]=3)[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[CH3:25][Si](C)(C)[N-][Si](C)(C)C.[Na+].CI.O>O1CCCC1>[CH3:25][N:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[CH:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[CH2:8][CH2:9][C:10]([C:18]=23)=[C:11]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 2724254Sodium bis(trimethylsilyl)amide2×HCID 19348199HCID 19348199, compound

Product 1

HCID 19348240HCID 19348240, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A portion (55 mg) of the compound obtained in Example 226 was dissolved in anhydrous tetrahydrofuran (2 ml) and to the solution was added sodium hexamethyldisilazide (1.0 M tetrahydrofuran solution; 0.52 ml) under cooling with ice. After stirring for 30 minutes, methyl iodide (32.3 μl) was added to the mixture, followed by stirring for 15 minutes. After adding further sodium hexamethyldisilazide (1.0 M tetrahydrofuran solution; 0.35 ml), the mixture was stirred for 30 minutes. Then, methyl iodide (21.5 μl) was added and the mixture was stirred for additional 15 minutes. Water was added to the reaction mixture, followed by extraction with two portions of ethyl acetate. The organic layers were combined, washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by preparative TLC (ethyl acetate/hexane=1:2) to yield 35 mg (61%) of the titled compound as a pale yellow solid. Specific rotation: [α]D +21° (25° C., c0.75, chloroform)

Workup

  1. temperatureunder cooling with ice
  2. stirringby stirring for 15 minutes
  3. stirringthe mixture was stirred for 30 minutes
  4. stirringthe mixture was stirred for additional 15 minutes
  5. extractionfollowed by extraction with two portions of ethyl acetate
  6. washwashed with water and saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by preparative TLC (ethyl acetate/hexane=1:2)

Sources & evidence

ORD record
ord-a678638dd33f47b083f2d1a234dd54b9
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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