1,2-Dichloroethane → {4-[4-(Pyrrolidin-1-ylcarbonyl)-1,3-oxazol-2-yl]phenyl}methanol

HRID 1716860Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=2)=[CH:5][CH:4]=1.C(Cl)CCl.[CH:21]1[CH:22]=CC2N(O)N=[N:27][C:25]=2[CH:26]=1.N1CCCC1>CN(C=O)C>[N:27]1([C:14]([C:12]2[N:13]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[CH:8][CH:7]=3)[O:10][CH:11]=2)=[O:16])[CH2:22][CH2:21][CH2:26][CH2:25]1

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred solution of 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylic acid (0.99 g, 4.5 mmol) in DMF was treated sequentially with EDC (1.04 g, 5.4 mmol), HOBt (0.67 g, 5.0 mmol and pyrrolidine (0.35 g, 5.0 mmol), stirred at 80° C. for 4 hours and evaporated to dryness. The resultant residue was dissolved in EtOAc and water. The layers were separated and the organic layer was washed successively with 1M HCl, water, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure The resultant residue was purified by flash chromatography (silica, EtOAc:hexanes 25%) to give the title product in 84% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 273 (MH+).

Workup

customevaporated to dryness
dissolutionThe resultant residue was dissolved in EtOAc
customThe layers were separated
washthe organic layer was washed successively with 1M HCl, water, saturated NaHCO3 and brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure The resultant residue
customwas purified by flash chromatography (silica, EtOAc:hexanes 25%)

Sources & evidence

ORD record: ord-c721f8f882734a99be033433945632e8
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803825B2

Reaction notes

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