Potassium Carbonate → HCID 86600748, compound

HRID 2252446Notes

Reaction equation

HRID 2252446 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10](=[O:18])[C@@H:9]2[CH2:19][CH2:20][C@H:21]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[C:4]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH:3]=1.CC1(C)C(C)(C)OB([C:53]2[CH:54]=[C:55]([P:59](=[O:64])([O:62][CH3:63])[O:60][CH3:61])[CH:56]=[CH:57][CH:58]=2)O1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C1(C)C=CC=CC=1>[Si:38]([O:37][C:4]1[CH:3]=[C:2]([C:53]2[CH:58]=[CH:57][CH:56]=[C:55]([P:59](=[O:64])([O:62][CH3:63])[O:60][CH3:61])[CH:54]=2)[CH:7]=[CH:6][C:5]=1[C@@H:8]1[C@@H:9]([CH2:19][CH2:20][C@H:21]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:10](=[O:18])[N:11]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 59643914HCID 59643914, compoundHCID 59643968HCID 59643968, compound

Product 1

HCID 86600748HCID 86600748, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

(3R,4S)-4-(4-Bromo-2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-2-one (0.080 g, 0.11 mmol), crude dimethyl [3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phosphonate (0.054 g total, 0.030 g calculated, 0.096 mmol) and aqueous 2 M potassium carbonate (0.12 mL, 0.24 mmol) were mixed in ethanol (1.0 mL) and toluene (3.0 mL). The solution was deoxygenated by bubbling nitrogen through the mixture for 5 min while stirring. Tetrakis(triphenylphosphine)palladium(0) (0.05 g) was added and the reaction was heated for 3 h at 70° C. under an atmosphere of nitrogen. The reaction was cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated by rotary evaporation under reduced pressure. The product was purified by chromatography over silica gel using ethyl acetate-hexane (gradient: 10% ethyl acetate to 80%) to afford dimethyl (3′-{[tert-butyl(dimethyl)silyl]oxy}-4′-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}biphenyl-3-yl)phosphonate as a colorless syrup (0.065 g, 84%). 1H NMR (300 MHz, CDCl3) δ 6.9-8.0 (m, 16H), 5.09 (d, J=2.2 Hz, 1H), 4.64 (d, J=6.1 Hz, 1H), 3.79 (d, J=2.4 Hz, 3H), 3.76 (d, J=2.4 Hz, 3H), 3.05-3.15 (m, 1H), 1.8-2.0 (m, 4H), 1.06 (s, 9H), 0.85 (s, 9H), 0.36 (s, 3H), 0.33 (s, 3H), 0.00 (s, 3H), −0.20 (s, 3H) ppm

Workup

  1. customThe solution was deoxygenated
  2. customby bubbling nitrogen through the mixture for 5 min
  3. additionTetrakis(triphenylphosphine)palladium(0) (0.05 g) was added
  4. temperatureThe reaction was cooled to room temperature
  5. additiondiluted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated by rotary evaporation under reduced pressure
  9. customThe product was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-374f21915e044dc68a5def8f035a697f
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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