Hydrochloric Acid → HCID 18766499, compound

HRID 480705Notes

Reaction equation

[NH2:1][C:2]([CH2:4][CH2:5][C:6]1[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=1[O:8][C:9]([CH3:18])([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=O.Cl.C(N)C.C(OCC)(=O)C>O1CCCC1>[NH2:1][CH2:2][CH2:4][CH2:5][C:6]1[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=1[O:8][C:9]([CH3:17])([CH3:18])[C:10]([O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:11]

Participants

Conditions

Temperature: 50 °C

Procedure

tert-Butyl 2-[2-(2-aminocarbonylethyl)phenoxy]-2-methylpropionate (2.7 g, 8.68 mmol) was dissolved in tetrahydrofuran (5 mL). Subsequently, under nitrogen atmosphere, borane-tetrahydrofuran complex in tetrahydrofuran solution [1.0M BH3-THF in THF (26.1 mL, 26.1 mmol)] was added thereto, the mixture was stirred for three hours at 50° C. Thereafter, concentrated hydrochloric acid was gradually added thereto at 0° C. The resultant mixture was stirred for one hour at room temperature and made basic with an aqueous ethylamine solution. Ethyl acetate was added thereto. The mixture was sequentially washed with water and saturated brine, followed by drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=30/1), whereby the target compound was obtained (1.44 g, 4.91 mmol, 57%).

Workup

customat 0° C
washThe mixture was sequentially washed with water and saturated brine
dry with materialby drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=30/1), whereby the target compound
customwas obtained (1.44 g, 4.91 mmol, 57%)

Sources & evidence

ORD record: ord-ff0aaa4ecbdf4e39b9df905ea014ca64
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653334B1

Reaction notes

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