Dimethylamine → HCID 54210754, compound

HRID 849849Notes

Reaction equation

HRID 849849 reaction equation
C(OC([CH2:8][NH:9][C@H:10]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:11][O:12][CH2:13][C:14](O)=[O:15])=O)(C)(C)C.ON1[C:29]2[N:30]=[CH:31]C=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CNC.C(O)C>CN(C)C=O.C(OCC)(=O)C.O>[CH3:29][N:30]([CH3:31])[C:14](=[O:15])[CH2:13][O:12][CH2:11][C@H:10]([NH:9][CH3:8])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

9

Reactant 5

HCID 674DimethylamineHCID 702EthanolHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54241244HCID 54241244, compound

Product 1

HCID 54210754HCID 54210754, compoundYield 49.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

((2R)-2-((tert-Butoxycarbonyl)methylamino)-3-phenylpropoxy)acetic acid (0.37 g, 1.14 mmol) and 1-hydroxy-7-azabenzotriazole (0.26 g, 1.14 mmol) were dissolved in N,N-dimethylformamide (7 ml). N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.26 g, 1.37 mmol) was added. The solution was stirred for 30 min. A 33% solution of dimethylamine in ethanol (0.33 ml, 1.26 mmol) was added. The solution was stirred over night. Water (20 ml) and ethyl acetate (15 ml) were added. The organic phase was washed with a 1M solution of sodium hydrogensulfate (30 ml) and a saturated solution of sodium hydrogencarbonate (30 ml). It was dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by column chromatography on silica (15 g) using ethyl acetate and dichloromethane (1:1) as eluent. This product was dissolved in dichloromethane (3 ml) and was cooled to 0° C. Trifluoroacetic acid (1 ml) was added. The solution was stirred at 0° C. for 20 min. The solvent was removed in vacuo. The residue was dissolved in dichloromethane (10 ml) and 1N sodium hydroxide solution (10 ml). The phases were separated. The aqueous phase was extracted with dichloromethane (4×10 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo to give 140 mg of crude N,N-dimethyl-2-((2R)-2-methylamino-3-phenylpropoxy)acetamide, which was used for further syntheses.

Workup

  1. stirringThe solution was stirred over night
  2. washThe organic phase was washed with a 1M solution of sodium hydrogensulfate (30 ml)
  3. dry with materialIt was dried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customThe crude product was purified by column chromatography on silica (15 g)
  6. dissolutionThis product was dissolved in dichloromethane (3 ml)
  7. additionTrifluoroacetic acid (1 ml) was added
  8. stirringThe solution was stirred at 0° C. for 20 min
  9. customThe solvent was removed in vacuo
  10. dissolutionThe residue was dissolved in dichloromethane (10 ml)
  11. customThe phases were separated
  12. extractionThe aqueous phase was extracted with dichloromethane (4×10 ml)
  13. dry with materialThe combined organic layers were dried over magnesium sulfate
  14. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-342f78ca3a54469a810dad25f49ff60e
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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