Ethanolamine → HCID 5730364, compound

HRID 1099583Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][OH:4].C1(C)C=CC=CC=1.[CH2:12]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:24][C:25](=[O:39])[C:26](=[CH:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH:36]([CH3:38])[CH3:37])=[CH:31][CH:30]=3)[N:27]=2)=[CH:19][CH:18]=1)[CH:13]([CH3:15])[CH3:14]>O>[OH:4][CH2:3][CH2:2][NH:1][C:25](/[C:26](/[NH:27][C:23](=[O:24])[C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:22][CH:21]=1)=[CH:28]\[C:29]1[CH:30]=[CH:31][C:32]([O:35][CH:36]([CH3:38])[CH3:37])=[CH:33][CH:34]=1)=[O:39]

Participants

Conditions

Temperature: 50 °C

Procedure

2-Aminoethanol (50 μL, 0.828 mmol) was added to a solution of toluene (2.0 mL) containing 2-(4-isobutoxyphenyl)-4-(4-isopropoxybenzylidene)-1,3-oxazol-5(4H)-one (151 mg, 0.398 mmol, a mixture of 4E isomer/4Z isomer=4.6/1) prepared in Example 103 (103a). The mixture was stirred at 50° C. for 15 minutes, and then water was added to this reaction solution. The resulting mixture was extracted with ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by thin layer chromatography for separation (ethyl acetate) to give 37 mg of the title compound (white solid, yield: 21%). [In addition, 53 mg of the corresponding Z isomer of the title compound (white solid, yield: 30%) was given.]

Workup

extractionThe resulting mixture was extracted with ethyl acetate
washwashed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe resulting residue was purified by thin layer chromatography for separation (ethyl acetate)

Sources & evidence

ORD record: ord-e1939a554bac4c789f4e8c57ba5d2ee6
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143446B2

Reaction notes

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