tert-Butanol → HCID 68582591, compound
Reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1C(O)=O.C([N:15]([CH2:18]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.[C:37]([OH:41])([CH3:40])([CH3:39])[CH3:38]>>[C:37]([O:41][C:18](=[O:27])[NH:15][C:3]1[CH:7]=[CH:8][C:9]([F:12])=[C:10]([Cl:11])[C:2]=1[Cl:1])([CH3:40])([CH3:39])[CH3:38]Participants
Procedure
To an oven-dried, N2-purged, 250-mL, round-bottomed flask containing a magnetic stir bar was added the product of Example 192A (3.14 g, 15.0 mmol). Anhydrous t-butanol (50 mL) was added via syringe. Triethylamine (2.62 mL, 1.90 g, 18.75 mmol) was added via syringe. Diphenylphosphorylazide (3.45 mL, 4.40 g, 16.5 mmol) was added via syringe. A reflux condenser with N2-inlet was attached and a heating mantle was applied. The golden solution was heated to reflux and stirred for 8 hours. After cooling to room temperature, the solvent/volatiles were removed by rotary evaporator to give a thick golden oil. The product was purified by flash chromatography (silica gel: 10% ethyl acetate, 90% hexanes—product Rf˜0.6) to give a 3.57 g (85%) of the title compound as a white powder. MS (ESI−) m/z 278.0 (M−H); 1H NMR (DMSO-d6) δ 1.45 (s, 9H), 7.42 (dd, J=9.0, 9.0 Hz, 1H), 7.54 (dd, J=9.2, 5.8 Hz, 1H), 8.95 (br s, 1H).
Workup
- customTo an oven-dried, N2-purged
- addition250-mL, round-bottomed flask containing a magnetic stir bar
- customA reflux condenser with N2-inlet was attached
- temperatureThe golden solution was heated
- temperatureto reflux
- customthe solvent/volatiles were removed by rotary evaporator
- customto give a thick golden oil
- customThe product was purified by flash chromatography (silica gel: 10% ethyl acetate, 90% hexanes—product Rf˜0.6)
Sources & evidence
- ORD record
- ord-299f830019e741e8aeb4537b25f1b9df
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07704997B1
Reaction notes
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