tert-Butyl acrylate → HCID 68162179, compound

HRID 2366887Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][NH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[CH:16]=[CH2:17].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[CH:12][N:13]([CH2:17][CH2:16][C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-(4-nitrophenyl)-1H-imidazole (for a preparation see Intermediate 120) (3.5 g, 18.5 mmol), 1,1-dimethylethyl 2-propenoate (2.37 g, 2.71 mL, 18.5 mmol) and DBU (2.82 g, 2.79 mL, 18.5 mmol) in DMF (50 mL) was stirred at 50° C. for 16 h then was cooled to room temperature and partitioned between AcOEt (100 mL) and water (100 mL). The layers were separated and the organic phase was washed with water then brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 25 to 50% AcOEt in hexanes) gave 1,1-dimethylethyl 3-[4-(4-nitrophenyl)-1H-imidazol-1-yl]propanoate (2.6 g, 8.19 mmol, 44%) as an orange solid. LCMS (method G): Retention time 0.90 min, [M+H]+=318.0

Workup

temperaturethen was cooled to room temperature
custompartitioned between AcOEt (100 mL) and water (100 mL)
customThe layers were separated
washthe organic phase was washed with water
dry with materialbrine, dried over MgSO4
concentrationconcentrated in vacuo
customPurification of the residue by flash chromatography on silica gel (gradient: 25 to 50% AcOEt in hexanes)

Sources & evidence

ORD record: ord-e1f287a916df474794d50fe7df05a291
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697725B2

Reaction notes

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