Water → HCID 18766429, compound

HRID 480696Notes

Reaction equation

HRID 480696 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[O:8][C:9]([CH3:18])([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].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.O>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:6]=[C:7]([CH:19]=[CH:20][CH:21]=1)[O:8][C:9]([CH3:18])([CH3:17])[C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 18766464HCID 18766464, compound

Product 1

HCID 18766429HCID 18766429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 2-[3-(3-aminopropyl)phenoxy]-2-methylpropionate (167 mg, 0.57 mmol) was dissolved in tetrahydrofuran (3.0 mL). Subsequently, diisopropylethylamine (73.6 mg, 0.57 mmol) and then 2-chlorobenzoxazole (96.2 mg, 0.63 mmol) were added dropwise thereto, and the mixture was stirred for four hours at room temperature. Water was added thereto, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, followed by drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (n-hexane/ethyl acetate=3/1), whereby the target compound was obtained (173 mg, 74%).

Workup

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialby drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (n-hexane/ethyl acetate=3/1), whereby the target compound
  4. customwas obtained (173 mg, 74%)

Sources & evidence

ORD record
ord-00a8e912a4cb454a816e91fdfae50c9a
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

Loading…