4-Methylmorpholine → HCID 67092960, compound

HRID 1261856Notes

Reaction equation

HRID 1261856 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][N:14]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:15][CH2:16][C:17](OC(C)(C)C)=[O:18])[CH2:11][CH2:10][C@@H:9]1[CH2:34][CH:35]=[CH2:36])=O)(C)(C)C.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>Cl>[CH2:27]([O:26][C:24]([N:14]1[CH2:15][CH2:16][C:17](=[O:18])[N:8]2[C@@H:9]([CH2:34][CH:35]=[CH2:36])[CH2:10][CH2:11][C@H:12]2[CH2:13]1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67092671HCID 67092671, compound

Product 1

HCID 67092960HCID 67092960, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (2R,5S)-2-allyl-5-{[benzyloxycarbonyl-(2-tert-butoxycarbonyl-ethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (875 mg, 1.74 mmol) in hydrogen chloride solution (4 M in 1,4-dioxane) was stirred for 21/2 h at room temperature, then concentrated in vacuo. The residue was taken up in N,N-dimethylformamide (10 mL), then 4-methylmorpholine (528 mg, 5.23 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (993 mg, 2.61 mmol) were added. The reaction mixture was stirred for 16 h at room temperature, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) afforded the title compound (479 mg, 84%). Colourless gum, MS: 329.4 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-759eb2388b9c4a2b86994ca26ce742a1
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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