Hydrochloric Acid → HCID 18766466, compound

HRID 480698Notes

Reaction equation

[CH2:1]([NH:4][C:5]([CH2:7][CH2:8][C:9]1[CH:25]=[CH:24][C:12]([O:13][C:14]([CH3:23])([CH3:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:11][CH:10]=1)=O)[CH2:2][CH3:3].Cl.C(N)C>O1CCCC1>[CH2:1]([NH:4][CH2:5][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][C:14]([CH3:23])([CH3:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:24][CH:25]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

tert-Butyl 2-[4-[2-(N-n-propylaminocarbonyl)ethyl]phenoxy]-2-methylpropionate (4.0 g, 11.4 mmol) was dissolved in tetrahydrofuran (10 mL). 1.0M Borane-tetrahydrofuran complex in tetrahydrofuran solution (34.3 mL, 34.3 mmol) was added dropwise, the mixture was stirred for three hours at 50° C. Concentrated hydrochloric acid was added under ice-cooling, the mixture was stirred for three hours at room temperature. Aqueous 80% ethylamine solution was added dropwise under ice-cooling, and the 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 (chloroform/methanol=50/1), whereby the target compound was obtained (2.3 g, 59%).

Workup

temperaturecooling
stirringthe mixture was stirred for three hours at room temperature
temperaturecooling
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialby drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=50/1), whereby the target compound
customwas obtained (2.3 g, 59%)

Sources & evidence

ORD record: ord-ddc6a80122f1422a82c8fcda686f51bd
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653334B1

Reaction notes

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