Triethylamine → HCID 15519729, compound

HRID 635451Notes

Reaction equation

HRID 635451 reaction equation
[CH2:1]([O:3][CH:4]([O:6][CH:7]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:9][C:8]1=[O:17])[CH3:5])[CH3:2].C(N(CC)CC)C.[N:25]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:25]1([C:31]([N:9]2[C@@H:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C@@H:7]([O:6][CH:4]([O:3][CH2:1][CH3:2])[CH3:5])[C:8]2=[O:17])=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 159320623-(1-Ethoxyethoxy)-4-phenylazetidin-2-one

Product 1

HCID 15519729HCID 15519729, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 30 mg (0.13 mmol) of 3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone 6 in 2 mL of CH2Cl2, 2 mg of DMAP and 0.05 mL of triethylamine was added at room temperature. After 5 min, 22.9 mg (0.15 mmol) of morpholinecarbonyl chloride was added. The reaction mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with 20 mL of CH2Cl2 and the organic layer was washed two times with brine, dried over Na2CO3 and concentrated. The crude solid product was purified by chromatography on silica gel to yield pure 7f: 87%; pale yellow oil; 1H NMR (250 MHz, CDCl3) δ [0.90 (d, J=5.3 Hz), 1.01 (d, J=5.3 Hz) (3H)], [1.04 (t, J=7.1 Hz), 1.18 (t, J=7.1 Hz)] (3H), 3.20 (m, 4H), [3.28 (m), 3.53 (m), 3.67 (m) (2H)], 3.60 (m, 4H), [4.41 (g, J=5.3 Hz), 4.63 (q, J=5.3 Hz) (1H)], [5.07 (d, J=5.8 Hz), 5.08 (d, J=5.8 Hz) (1H)], [5.29 (d, J=5.8 Hz), 5.32 (d, J=5.8 Hz) (1H)], 7.23-7.27 (m, 5H).

Workup

  1. washthe organic layer was washed two times with brine
  2. dry with materialdried over Na2CO3
  3. concentrationconcentrated
  4. customThe crude solid product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2d239493da604469a4a1e1b7131507b6
Source dataset
uspto-grants-2001_02
Patent number
US06187916B1

Reaction notes

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