Ethyl pent-2-yn-1-oate → (S)-5-ethyl-2-[4-(3,3,5,5-tetramethyl-cyclohexyl)-phenoxymethyl]-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one
Reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([C:10]2[CH:23]=[CH:22][C:13]([O:14][CH2:15][CH:16]3[O:20][C:19]([NH2:21])=[N:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:3]1.C1O[C@H]1CCl.CC1(C)CC(C)(C)C[CH:33]([C:39]2C=C[C:42]([OH:45])=[CH:41][CH:40]=2)C1.C(OCC)(=O)C#CCC>C(O)C>[CH2:39]([C:40]1[N:18]2[CH2:17][C@@H:16]([CH2:15][O:14][C:13]3[CH:12]=[CH:11][C:10]([CH:4]4[CH2:5][C:6]([CH3:8])([CH3:9])[CH2:7][C:2]([CH3:24])([CH3:1])[CH2:3]4)=[CH:23][CH:22]=3)[O:20][C:19]2=[N:21][C:42](=[O:45])[CH:41]=1)[CH3:33]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-[4-(3,3,5,5-tetramethyl-cyclohexyl)-phenoxymethyl]-4,5-dihydro-oxazol-2-ylamine (0.15 g, 0.454 mmol), prepared in accordance with the procedures described in Steps 1 and 2 of Example 1 and starting from R-epichlorohydrin and 4-(3,3,5,5-tetramethyl-cyclohexyl)-phenol (prepared using the same procedure as in step 1 of Example 74), in ethanol (5 mL) was added ethyl 2-pentynoate (0.086 g, 0.681 mmol). The reaction mixture was heated at reflux for 14 hrs and then cooled to room temperature. The reaction mixture was concentrated, loaded onto a silica gel column, and eluted with 4% methanol/methylene chloride to afford 23 mg of (S)-5-ethyl-2-[4-(3,3,5,5-tetramethyl-cyclohexyl)-phenoxymethyl]-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one.
Workup
- customprepared
- temperatureThe reaction mixture was heated
- temperatureat reflux for 14 hrs
- concentrationThe reaction mixture was concentrated
- washeluted with 4% methanol/methylene chloride
Sources & evidence
- ORD record
- ord-0d2cc9c955714c0eb05903843caa03b2
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642603B2
Reaction notes
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