Triethylamine → Ethyl 5-[(morpholin-4-yl)methyl]-1,2-oxazole-3-carboxylate

HRID 872782Notes

Reaction equation

HRID 872782 reaction equation
[CH3:1][CH2:2][O:3][C:4](/[C:6](/Cl)=[N:7]\[OH:8])=[O:5].[CH2:10]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[C:11]#[CH:12].C(N(CC)CC)C>C1(C)C=CC=CC=1.O>[O:16]1[CH2:17][CH2:18][N:13]([CH2:10][C:11]2[O:8][N:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:12]=2)[CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4129414-(2-Propyn-1-yl)morpholineHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate

Product 1

HCID 23006302Ethyl 5-[(morpholin-4-yl)methyl]-1,2-oxazole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To the solution of ethyl chlorooximidoacetate (0.588 g, 3.88 mmol) and 4-(prop-2-ynyl)morpholine (0.971 g, 7.76 mmol) in toluene (5 mL) was added solution of triethylamine (0.54 mL, 3.88 mmol) in toluene (5 mL) dropwise. The resultant mixture was stirred at RT for 5 h. After the completion of the reaction as evidenced by LC-MS, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic solvent was then dried over anhydrous sodium sulfate and evaporated. The crude product was purified by Combiflash (Heptane:EtOAc eluent). Yield 0.2 g. 1H NMR (400 MHz; MeOD): δ 1.38 (t, 3H), 2.53 (m, 4H), 3.69 (m, 4H), 3.78 (d, 2H), 4.41 (q, 2H), 6.73 (m, 1H).

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic solvent was then dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe crude product was purified by Combiflash (Heptane:EtOAc eluent)

Sources & evidence

ORD record
ord-7308ad297900412db1a4865e1737e70c
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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