Triethylamine → HCID 16747947, compound

HRID 1350222Notes

Reaction equation

HRID 1350222 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C@H:8]([CH2:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:9][C:10]([OH:12])=[O:11])[O:5][N:4]=1.CCN(CC)CC.[CH3:29][C:30]([O:33][C:34](ON=C(C1C=CC=CC=1)C#N)=[O:35])([CH3:32])[CH3:31]>O1CCOCC1.O>[C:30]([O:33][C:34]([NH:1][CH2:2][C:3]1[N:7]=[C:6]([C@H:8]([CH2:13][CH2:14][CH2:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:9][C:10]([OH:12])=[O:11])[O:5][N:4]=1)=[O:35])([CH3:32])([CH3:31])[CH3:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 60077637HCID 60077637, compound

Product 1

HCID 16747947HCID 16747947, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of (3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoic acid (preparation 163) (177 mg, 0.53 mmol) and Et3N (186 μl, 1.33 mmol) in dioxan (500 μl) and H2O (500 μl) was treated with Boc-ON (145 mg, 0.58 mmol) and stirred at room temperature for 18 hours. The reaction mixture was diluted with H2O and extracted with EtOAc (×2). The organic extracts were combined and the solvent removed under reduced pressure. The crude material was purified on a silica column eluting with DCM:MeOH (100:0) gradually changing to (90:10) to afford the title compound as a colourless gum (115 mg, 55%).

Workup

  1. extractionextracted with EtOAc (×2)
  2. customthe solvent removed under reduced pressure
  3. customThe crude material was purified on a silica column
  4. washeluting with DCM:MeOH (100:0)

Sources & evidence

ORD record
ord-82a6a8bc1e02423da664b79a268e6950
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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