4-Methylmorpholine → HCID 22244748, compound

HRID 891047Notes

Reaction equation

HRID 891047 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:12]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](O)=[O:19])(=[O:14])[CH3:13].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][CH:23]=[C:15]([C:12](=[O:14])[CH3:13])[CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 187201N-BOC-ethylenediamineHCID 2203243-Acetylbenzoic acid

Product 1

HCID 22244748HCID 22244748, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(t-Butoxycarbonyl)ethylenediamine 2 (5 mmol, 800 mg) was weighed directly into a clean dry flask, which was then tightly stoppered. 3-Acetylbenzoic acid 3 (5 mmol, 820 mg) was added directly to the amine in the flask. Under an inert atmosphere dry dimethylformamide (15 mL) was added to the flask. Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (5 mmol, 2.21 g) was added to the solution, and subsequently N-methylmorpholine (15 mmol, 1.51 g, 1.7 mL) was added to the solution, and the mixture was allowed to stir for 2-3 hrs. The reaction mixture was quenched by the addition of 15 mL of water to the reaction flask, and partitioned between water (300 mL) and ethyl acetate (300 mL). The organic phase was washed successively with saturated sodium bicarbonate (200 mL), water (4×300 mL), and brine (200 mL) and then dried over anhydrous sodium sulfate. Filtering off the drying agent and concentration of the organic phase to ˜10-15 mL yielded a tan solid. Hexanes (˜30 mL) were added and the mixture gently heated to reflux. Upon cooling semicrystalline product was precipitated as a white powder. The product was collected by filtration and dried. Yield 775 mg, 51%.

Workup

  1. additionwas added to the solution
  2. customThe reaction mixture was quenched by the addition of 15 mL of water to the reaction flask
  3. custompartitioned between water (300 mL) and ethyl acetate (300 mL)
  4. washThe organic phase was washed successively with saturated sodium bicarbonate (200 mL), water (4×300 mL), and brine (200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationFiltering off the drying agent and concentration of the organic phase to ˜10-15 mL
  7. customyielded a tan solid
  8. temperaturethe mixture gently heated to reflux
  9. temperatureUpon cooling semicrystalline product
  10. customwas precipitated as a white powder
  11. filtrationThe product was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-4f98fc35fc134b028da1d15b06df00c7
Source dataset
uspto-grants-2006_02
Patent number
US07001924B2

Reaction notes

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