Morpholine → HCID 25529914, compound

HRID 1620769Notes

Reaction equation

HRID 1620769 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C=O)C.O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@@H:12]([CH:13]([CH3:14])[CH3:15])[C:16]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 726987N-Carbobenzoxy-L-valineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 25529914HCID 25529914, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[(benzyloxy)carbonyl]-L-valine (1.26 g) and morpholine (0.479 g) and N-ethyl-N-(1-methylethyl)propan-2-amine (0.711 g) in DMF (20 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.90 g) at room temperature. The reaction mixture was stirred at room temperature overnight, the reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate/hexane, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure to give the title compound (1.53 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate/hexane
  7. customthe insoluble material was removed by filtration
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a738ef4c5ab64497bac01bbc2d2fc20d
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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