Ethyl Acetate → HCID 70059530, compound
Reaction equation
[C:1]([O:5][C:6](=[O:34])[CH:7]([NH:16][C:17](=[O:33])[CH:18]([NH:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.[H-].[Na+].C(OCC)(=O)C>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:34])[CH:7]([NH:16][C:17](=[O:33])[CH:18]([NH:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[CH:13][CH:14]=1)([CH3:3])([CH3:4])[CH3:2]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
A solution of the product from Example 24 (0.20 g, 0.42 mmol) and bromomethylcyclohexane (0.6 μL, 0.45 mmol) in DMF (2 mL) was added sodium hydride (60% in dispersion oil, 0.016 g, 0.42 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and warmed to room temperature. The reaction mixture was poured into a separatory funnel containing ethyl acetate (50 mL) and water (50 mL). The organic phase was collected, washed with brine, and dried. The residue was purified by chromatography (silica gel, ethyl acetate/hexane) to give the title compound (0.13 g).
Workup
- temperaturewarmed to room temperature
- additionThe reaction mixture was poured into a separatory funnel
- customThe organic phase was collected
- washwashed with brine
- customdried
- customThe residue was purified by chromatography (silica gel, ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-edf5193fab024fa1be3f5872f4158877
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06423689B1
Reaction notes
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