Ethyl Acetate → HCID 18766431, compound

HRID 480706Notes

Reaction equation

HRID 480706 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:21]=[CH:20][CH:19]=[CH:18][C:6]=1[O:7][C:8]([CH3:17])([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(N(C(C)C)CC)(C)C.Cl[C:32]1[O:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=1.C(OCC)(=O)C>O1CCCC1>[O:33]1[C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=[C:32]1[NH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:21]=[CH:20][CH:19]=[CH:18][C:6]=1[O:7][C:8]([CH3:16])([CH3:17])[C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 18766499HCID 18766499, compound

Product 1

HCID 18766431HCID 18766431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 2-[2-(3-aminopropyl)phenoxy]-2-methylpropionate (1.44 g, 4.9 mmol) was dissolved in tetrahydrofuran (5 mL). Subsequently, diisopropylethylamine (762 mg, 5.9 mmol) and then 2-chlorobenzoxazole (904 mg, 5.9 mmol) were added thereto, and the mixture was stirred overnight at room temperature. Ethyl acetate was added thereto. The resultant mixture was sequentially washed with water and saturated brine, followed by drying over sodium sulfate, filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=6/1), whereby the target compound was obtained (2.03 g, q.).

Workup

  1. washThe resultant mixture was sequentially washed with water and saturated brine
  2. dry with materialby drying over sodium sulfate, filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=6/1), whereby the target compound
  3. customwas obtained (2.03 g, q.)

Sources & evidence

ORD record
ord-57017e4facea4b7da72f35eb031457c6
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

Loading…