N,N-Dimethylglycine → HCID 101890027, compound

HRID 511051Notes

Reaction equation

HRID 511051 reaction equation
[CH2:1]1[CH2:31][O:30][C:3]2([CH2:20][CH2:19][C:18]3[C@@:5]([OH:29])([CH2:6][CH2:7][C@@H:8]4[C:17]=3[C@@H:16]([C:21]3[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=3)[CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C:12]3=[O:28])[CH2:4]2)[O:2]1.[NH:32]1[CH:36]=[CH:35][N:34]=[CH:33]1.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH2:1]1[CH2:31][O:30][C:3]2([CH2:20][CH2:19][C:18]3[C@@:5]([OH:29])([CH2:6][CH2:7][C@@H:8]4[C:17]=3[C@@H:16]([C:21]3[CH:26]=[CH:25][C:24]([N:32]5[CH:36]=[CH:35][N:34]=[CH:33]5)=[CH:23][CH:22]=3)[CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C:12]3=[O:28])[CH2:4]2)[O:2]1

Participants

6

Reactant 4

HCID 673N,N-DimethylglycineHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 101890023HCID 101890023, compound

Product 1

HCID 101890027HCID 101890027, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of compound 3 (9.7 g, 18 mmol), imidazole (1.4 g, 20 mmol), cuprous iodide (346 mg, 1.8 mmol), N, N-dimethyl glycine (374 mg, 3.6 mmol) and potassium carbonate (5 g, 36 mmol) in anhydrous DMSO (10 mL) was degassed three times applying vacuum and nitrogen and was immersed in to a preheated oil bath at 110° C. The reaction mixture was heated for 60 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (150 mL) and filtered through a Celite pad. The filtrate was transferred to a reparatory funnel and was washed with water, brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum to afford the crude product, which on purification by chromatography on SiO2 column eluting with 30% acetone in dichloromethane gave 7.6 g (91%) of required product 4 as a pale yellow solid.

Workup

  1. customwas degassed three times
  2. customwas immersed in to a preheated oil bath at 110° C
  3. temperatureThe reaction mixture was heated for 60 h
  4. additionthe reaction mixture was diluted with ethyl acetate (150 mL)
  5. filtrationfiltered through a Celite pad
  6. customThe filtrate was transferred to a reparatory funnel
  7. washwas washed with water, brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed under vacuum
  10. customto afford the crude product, which
  11. customon purification by chromatography on SiO2 column
  12. washeluting with 30% acetone in dichloromethane

Sources & evidence

ORD record
ord-4ee13f10cf57455092e60136367f6115
Source dataset
uspto-grants-2015_08
Patent number
US09096641B2

Reaction notes

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