Ethanol → HCID 58276247, compound
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]([CH:26]3[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[CH2:28][CH2:27]3)[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:34]O.CC1C=CC(S(O)(=O)=O)=CC=1.O.C[CH2:49][OH:50]>>[CH3:32][C:29]1([CH3:33])[CH2:30][CH2:31][CH:26]([N:18]([CH2:17][CH2:16][O:15][C:12]2[CH:11]=[CH:10][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]4[N:34]=[CH:49][O:50][N:2]=4)[CH:4]=3)=[CH:14][CH:13]=2)[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:27][CH2:28]1Participants
Procedure
To a solution of 1,1-dimethylethyl {2-[(3′-cyano-4-biphenyl)oxy]ethyl}(4,4-dimethylcyclohexyl)carbamate (0.125 g; 0.279 mmol; step 1 above) in EtOH (2.5 mL) at room temperature was added a solution of hydroxylamine (0.25 mL of a 50 wt % aq solution). The mixture was stirred 70 h at room temperature and volatiles were removed in vacuo (1×PhMe chase). The residue was dissolved in trimethyl orthoformate (2 mL), TsOH.H2O (0.0025 g; 0.013 mmol) was added and the mixture was heated at 100° C. in a sealed vial for 1 h. Upon cooling, the mixture was adsorbed onto a small amount of silica gel and purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless gum. LC/MS (method A) tR 3.34 min, m/z 492 (M+H, 5%), 514 (M+Na, 100%), 392 ([M-Boc]+H, 53%).
Workup
- customvolatiles were removed in vacuo (1×PhMe chase)
- dissolutionThe residue was dissolved in trimethyl orthoformate (2 mL)
- temperaturethe mixture was heated at 100° C. in a sealed vial for 1 h
- temperatureUpon cooling
- custompurified by flash chromatography (EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-a64522bfa054426b8ab3043fbbb45120
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822518B2
Reaction notes
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