Phenylacetic Acid → N-[1-(4-ethyloxazol-2-yl)-2-(4-nitrophenyl)ethyl]-2-phenylacetamide

HRID 1046622Notes

Reaction equation

[CH2:1]([C:3]1[N:4]=[C:5]([C@@H:8]([NH2:19])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[O:6][CH:7]=1)[CH3:2].[C:20]1([CH2:26][C:27](O)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C=O)C.O>[CH2:1]([C:3]1[N:4]=[C:5]([CH:8]([NH:19][C:27](=[O:28])[CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[O:6][CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (S)-1-(4-ethyloxazol-2-yl)-2-(4-nitrophenyl)ethanamine, 65, (2.9 g, 11 mmol), phenylacetic acid (1.90 g, 14 mmol) and 1-hydroxybenzotriazole (HOBt) (0.94 g, 7.0 mmol) in DMF (100 mL) at 0° C., is added 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide (EDCI) (2.68 g, 14 mmol) followed by triethylamine (6.0 mL, 42 mmol). The mixture is stirred at 0° C. for 30 minutes then at room temperature overnight. The reaction mixture is diluted with water and extracted with EtOAc. The combined organic phase is washed with 1 N aqueous HCl, 5% aqueous NaHCO3, water and brine, and dried over Na2SO4. The solvent is removed in vacuo to afford the desired product which is used without further purification.

Workup

customat room temperature
customovernight
extractionextracted with EtOAc
washThe combined organic phase is washed with 1 N aqueous HCl, 5% aqueous NaHCO3, water and brine
dry with materialdried over Na2SO4
customThe solvent is removed in vacuo

Sources & evidence

ORD record: ord-3548dd4cd3e14e71adbd54cdebc77b64
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569348B2

Reaction notes

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