Ethyl Acetate → Ethyl 2-[3-[2-(N-Benzoxazol-2-yl)aminoethyl]phenoxy]-2-methylpropionate

HRID 480714Notes

Reaction equation

HRID 480714 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(N(C(C)C)CC)(C)C.Cl[C:29]1[O:30][C:31]2[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=2[N:33]=1.C(OCC)(=O)C>O1CCCC1>[O:30]1[C:31]2[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=2[N:33]=[C:29]1[NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 187664062-[3-(2-Amino-ethyl)-phenoxy]-2-methyl-propionic acid ethyl ester

Product 1

HCID 18766465Ethyl 2-[3-[2-(N-Benzoxazol-2-yl)aminoethyl]phenoxy]-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[3-(2-aminoethyl)phenoxy]-2-methylpropionate (1.1 g, 4.38 mmol) was dissolved in tetrahydrofuran (22 mL). Subsequently, diisopropylethylamine (1.14 mL, 6.57 mmol) and then 2-chlorobenzoxazole (611 mL, 5.26 mmol) were added thereto, and the mixture was stirred under argon atmosphere for 14 hours at room temperature. Ethyl acetate was added to the reaction mixture. Washing was performed sequentially with water and saturated brine, followed by drying over sodium sulfate. Thereafter, the reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=10/1), whereby the target compound was obtained (900 mg, 2.44 mmol, 55.8%).

Workup

  1. washWashing
  2. dry with materialby drying over sodium sulfate
  3. filtrationThereafter, the reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=10/1), whereby the target compound
  4. customwas obtained (900 mg, 2.44 mmol, 55.8%)

Sources & evidence

ORD record
ord-0fcdfda1276f4bdd92295fb9155cc06b
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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