4-Methylmorpholine → HCID 60077596, compound

HRID 1350219Notes

Reaction equation

HRID 1350219 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C@H:8]([CH2:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[O:5][N:4]=1.[CH3:26][O:27][CH2:28][C:29](O)=[O:30].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[CH:20]1([CH2:19][CH2:18][CH2:17][C@@H:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][NH:1][C:29](=[O:30])[CH2:28][O:27][CH3:26])[N:7]=2)[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 12251Methoxyacetic AcidHCID 757711-HydroxybenzotriazoleHCID 16747946tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate

Product 1

HCID 60077596HCID 60077596, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate (preparation 18) (206 mg, 0.57 mmol) and methoxyacetic acid (48 μl, 0.63 mmol) in DCM (5 ml) was treated with a solution of WSCDI (120 mg, 0.63 mmol), HOBt (85 mg, 0.63 mmol) and NMM (69 μl, 0.63 mmol) in DCM (10 ml) and stirred at room temperature for 18 hours. The reaction mixture was washed with sat. NaHCO3 solution followed by brine, dried over MgSO4 and filtered. The solvent was removed under reduced pressure. The residue was purified on a silica column eluting with Et2O to afford the title compound as a colourless oil (230 mg, 93%).

Workup

  1. washThe reaction mixture was washed with sat. NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified on a silica column
  6. washeluting with Et2O

Sources & evidence

ORD record
ord-fbf3b8626d54493c8a2f61bf4108f412
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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