Acetone → HCID 86759919, compound
Reaction equation
N12CCCN=C1CC[CH2:4][CH2:3][CH2:2]2.[Cl:12][C:13]1[CH:14]=[C:15]([CH2:19][CH:20]([OH:39])/[CH:21]=[CH:22]/[C@H:23]2[CH2:28][CH2:27][CH2:26][C:25](=O)[N:24]2[CH2:30][CH2:31][CH2:32][CH2:33][O:34][CH2:35][C:36]([OH:38])=[O:37])[CH:16]=[CH:17][CH:18]=1.IC(C)C.CC(C)=[O:46]>>[CH:3]([O:38][C:36](=[O:37])[CH2:35][O:34][CH2:33][CH2:32][CH2:31][CH2:30][N:24]1[CH2:25][CH2:26][CH2:27][C:28](=[O:46])[C@H:23]1/[CH:22]=[CH:21]/[CH:20]([OH:39])[CH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[CH:14]=1)([CH3:4])[CH3:2]Participants
5
Procedure
1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU, 16 μL, 0.11 mmol) was added to a solution of (4-{(R)-2-[(E)-4-(3-chlorophenyl)-3-hydroxy-but-1-enyl]-6-oxo -piperidin-1-yl)-butoxy)-acetic acid (29 mg, 0.071 mmol) in acetone (0.5 mL). After 5 min, 2-iodopropane (35 μL, 0.35 mmol) was added. After 17 h, the reaction mixture was concentrated in vacuo, EtOAc (15 mL) was added and the resultant mixture was washed with 0.5 M aqueous HCl (5 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL). The organic phase was then dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2 →5% MeOH/CH2Cl2, gradient) afforded 16 mg (50%) of the title compound.
Workup
- waitAfter 17 h
- concentrationthe reaction mixture was concentrated in vacuo, EtOAc (15 mL)
- additionwas added
- washthe resultant mixture was washed with 0.5 M aqueous HCl (5 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL)
- dry with materialThe organic phase was then dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification of the residue by flash column chromatography on silica gel (CH2Cl2 →5% MeOH/CH2Cl2, gradient)
Sources & evidence
- ORD record
- ord-422e7209ee9744f89c2e4d6ff3b3e89a
- Source dataset
- uspto-grants-2005_12
- Patent number
- US06977260B2
Reaction notes
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