Ethanol → HCID 25057044, compound
Reaction equation
[CH3:1][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C@H:28]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:29][C:30]([O:32]C)=[O:31])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C1COCC1.CCO.[OH-].[Na+]>>[CH3:4][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([C@H:28]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:29][C:30]([OH:32])=[O:31])=[CH:26][CH:27]=2)=[CH:7][CH:6]=1)([CH3:1])[CH3:3]Participants
5
Procedure
To a stirred solution of 37.2 (0.077 g, 0.15 mmol) in THF (2 mL, 0.2 mmol) and EtOH (2 mL, 0.2 mmol) at 23° C. was added a solution of 1 M sodium hydroxide (1.00 mL, 1.0 mmol). The resulting reaction mixture was stirred for 19 hours. The resulting reaction was concentrated in vacuo. 1 N HCl was added to bring the pH to 1, and the resulting mixture was extracted EtOAc, dried over MgSO4, filtered, and concentrated. The product thus obtained was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford compound 37 (60 mg, 80% yield) as a colorless oil. MS ESI (neg.) m/e: 983.5 (2M−H)+, 491.3 (M−H)+.
Workup
- customThe resulting reaction mixture
- customThe resulting reaction
- concentrationwas concentrated in vacuo
- addition1 N HCl was added
- extractionthe resulting mixture was extracted EtOAc
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe product thus obtained
- customwas purified by silica gel flash chromatography (0-20% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-698521c7f8bc4212bf53591a4503f596
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07572934B2
Reaction notes
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