Formic Acid → HCID 58392798, compound
Reaction equation
Cl.[F:2][C@@:3]12[C@:16]3([CH3:17])[C:11](=[CH:12][C:13](=[O:18])[CH:14]=[CH:15]3)[C@@H:10]([F:19])[CH2:9][C@H:8]1[C@@H:7]1[CH2:20][C@@H:21]3[C@:25]([C:26](=[O:29])[CH2:27][F:28])([C@@:6]1([CH3:30])[CH2:5][C@@H:4]2[OH:31])[CH2:24][NH:23][CH2:22]3.[CH3:32][C:33]([CH3:38])([CH3:37])[CH2:34][CH:35]=O.C(O)=O>C(#N)C.CCOC(C)=O>[CH3:32][C:33]([CH3:38])([CH3:37])[CH2:34][CH2:35][N:23]1[CH2:24][C@:25]2([C:26](=[O:29])[CH2:27][F:28])[C@@H:21]([CH2:20][C@H:7]3[C@H:8]4[C@@:3]([F:2])([C@:16]5([CH3:17])[C:11]([C@@H:10]([F:19])[CH2:9]4)=[CH:12][C:13](=[O:18])[CH:14]=[CH:15]5)[C@@H:4]([OH:31])[CH2:5][C@@:6]32[CH3:30])[CH2:22]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 140 °C
Procedure
In a closed vessel, compound 166 (180 mg, 0.391 mmol), 3,3-dimethylbutanal (0.196 ml, 1.565 mmol) and TEA (0.055 ml, 0.391 mmol) are dissolved in acetonitrile (4 ml). Formic acid (0.120 ml, 3.13 mmol) is added and the mixture is heated under microwave irradiation for 15 minutes at 140° C. LC-MS shows that the reaction is complete. The reaction mixture is diluted with AcOEt and the organic phase is washed with a saturated solution of NaHCO3 and with brine. The organic layer is dried over Na2SO4 and filtered. The solvent is evaporated to give an orange oil which is purified by preparative HPLC (acetonitrile/water, neutral phase) to yield the title compound (55 mg, 0.108 mmol, 27.7% yield).
Workup
- washthe organic phase is washed with a saturated solution of NaHCO3 and with brine
- dry with materialThe organic layer is dried over Na2SO4
- filtrationfiltered
- customThe solvent is evaporated
- customto give an orange oil which
- customis purified by preparative HPLC (acetonitrile/water, neutral phase)
Sources & evidence
- ORD record
- ord-05bc13c3c6684ea696e1e66230d5ba65
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481517B2
Reaction notes
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