4-Methylmorpholine → HCID 60077611, compound

HRID 1350239Notes

Reaction equation

HRID 1350239 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.Br[CH2:27][C:28]([O:30][CH3:31])=[O:29].CN1CCOCC1>C1COCC1.CCOC(C)=O>[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][CH2:27][C:28]([O:30][CH3:31])=[O:29])[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 3

HCID 79724-MethylmorpholineHCID 60984Methyl bromoacetateHCID 16747946tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate

Product 1

HCID 60077611HCID 60077611, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate (preparation 18) (200 mg, 0.57 mmol) in THF (2 ml) was treated with methyl bromoacetate (55 μl, 0.57 mmol) and NMM (63 μl, 0.57 mmol) and stirred at room temperature, under a nitrogen atmosphere for 3 days. The reaction mixture was diluted with EtOAc and washed with H2O followed by brine, dried over anhydrous MgSO4 and filtered. The solvent was removed under reduced pressure. The crude material was purified on a silica column eluting with a solvent gradient of EtOAc:pentane (5:95) gradually changing to (50:50) to afford the title compound as a colourless oil (170 mg, 70%).

Workup

  1. washwashed with H2O
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. customThe crude material was purified on a silica column
  6. washeluting with a solvent gradient of EtOAc:pentane (5:95)

Sources & evidence

ORD record
ord-b881a00699d14a29a7f3ba22b3ffefc1
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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