Dimethylamine → HCID 25261081, compound

HRID 2246537Notes

Reaction equation

HRID 2246537 reaction equation
Br[CH2:2][CH2:3][CH2:4][Si:5]([CH3:35])([CH3:34])[CH2:6][CH2:7][C:8]1[C:20]2[CH2:19][N:18]3[C:13](=[CH:14][C:15]4[C@:25]([CH2:27][CH3:28])([OH:26])[C:24](=[O:29])[O:23][CH2:22][C:16]=4[C:17]3=[O:21])[C:12]=2[N:11]=[C:10]2[CH:30]=[CH:31][CH:32]=[CH:33][C:9]=12.C(=O)([O-])[O-].[K+].[K+].CC(O)(C)C.[CH3:47][NH:48][CH3:49]>O.O1CCCC1>[CH3:47][N:48]([CH3:49])[CH2:2][CH2:3][CH2:4][Si:5]([CH3:35])([CH3:34])[CH2:6][CH2:7][C:8]1[C:20]2[CH2:19][N:18]3[C:13](=[CH:14][C:15]4[C@:25]([CH2:27][CH3:28])([OH:26])[C:24](=[O:29])[O:23][CH2:22][C:16]=4[C:17]3=[O:21])[C:12]=2[N:11]=[C:10]2[CH:30]=[CH:31][CH:32]=[CH:33][C:9]=12

Participants

7

Reactant 4

HCID 674DimethylamineHCID 6386tert-ButanolHCID 11430Potassium CarbonateHCID 25260614HCID 25260614, compound

Product 1

HCID 25261081HCID 25261081, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Compound 11 (50 mg) and potassium carbonate (37 mg) in deionized water (1 mL) was stirred at room temperature for 30 min. To the resulting mixture, t-BuOH (1 mL) and 2 molar dimethylamine in tetrahydrofuran (0.14 mL) were added and stirred at room temperature for 24 hours. Finally, the reaction mixture was concentrated under vacuum and the resulting residue was dissolved in a mixture of acetic acid (10 mL) and trifluoroacetic acid (1 mL) and stirred at room temperature for 8 hours. The crude material was obtained by concentrating the acetic acid solution under vacuum and the residue was partitioned between 7% aqueous NaHCO3 solution (5 mL) and chloroform (2×10 mL). The combined organic layer was dried and concentrated and the residue was eluted on a silica gel column using 10% ethanol in dichloromethane to obtain the required product in 56% yield (26 mg).

Workup

  1. stirringstirred at room temperature for 24 hours
  2. concentrationFinally, the reaction mixture was concentrated under vacuum
  3. dissolutionthe resulting residue was dissolved in a mixture of acetic acid (10 mL) and trifluoroacetic acid (1 mL)
  4. stirringstirred at room temperature for 8 hours
  5. customThe crude material was obtained
  6. concentrationby concentrating the acetic acid solution under vacuum
  7. customthe residue was partitioned between 7% aqueous NaHCO3 solution (5 mL) and chloroform (2×10 mL)
  8. customThe combined organic layer was dried
  9. concentrationconcentrated
  10. washthe residue was eluted on a silica gel column

Sources & evidence

ORD record
ord-00f40f360f76447f9abb8e2041e8e4f1
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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