Acetonitrile → HCID 86680462, compound
Reaction equation
[CH2:1]=[C:2]([C:4]1[N:5]=[CH:6][C:7]([O:10][C@H:11]2[CH2:26][N:14]3[CH2:15][CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][C@@H:13]3[CH2:12]2)=[N:8][CH:9]=1)[CH3:3].[N+](=[CH2:29])=[N-].C(#N)C>O1CCCC1.C(OCC)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:26][N:14]4[CH2:15][CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:29][CH2:3]1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the product from Example 202B (40 mg, 0.111 mmol) in anhydrous tetrahydrofuran (1 mL) was added a 0.67 M solution of diazomethane in diethyl ether. The yellow solution was cooled to 0° C., and palladium(II) acetate (1 mg, 4.45 μmol) was added resulting in rapid gas evolution. More diazomethane solution (1 mL) was added dropwise, and the mixture was stirred at 0° C. for 30 minutes. The addition of 1 mL diazomethane solution was repeated several more times at 0° C. while monitoring reaction progress by LCMS (C18 silica gel using a 3 minute gradient of 0-100% acetonitrile in water (0.1% trifluoroacetic acid)). The reaction mixture was concentrated in vacuo and purified by column chromatography on silica gel using a solvent gradient of 0-50% ethyl acetate in hexanes. The title compound was obtained as a colorless oil that crystallized on standing (30 mg, 72%).
Workup
- customresulting in rapid gas evolution
- customat 0° C.
- concentrationThe reaction mixture was concentrated in vacuo
- custompurified by column chromatography on silica gel using a solvent gradient of 0-50% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-5a16530e9f754c69a4fa7703dee64e32
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08648074B2
Reaction notes
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