Potassium Carbonate → HCID 69257981, compound

HRID 2252451Notes

Reaction equation

HRID 2252451 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:37])[CH2:9][CH2:10][C@@H:11]2[C@@H:14]([C:15]3[CH:20]=[CH:19][C:18](B4OC(C)(C)C(C)(C)O4)=[CH:17][CH:16]=3)[N:13]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:12]2=[O:36])=[CH:4][CH:3]=1.[C:38]([O:41][C@@H:42]1[C@@H:47]([O:48][C:49](=[O:51])[CH3:50])[C@H:46]([O:52][C:53](=[O:55])[CH3:54])[C@@H:45]([CH2:56][O:57][C:58](=[O:60])[CH3:59])[O:44][C@H:43]1[C:61]1[CH:66]=[CH:65][CH:64]=[C:63](Br)[CH:62]=1)(=[O:40])[CH3:39].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:38]([O:41][C@@H:42]1[C@@H:47]([O:48][C:49](=[O:51])[CH3:50])[C@H:46]([O:52][C:53](=[O:55])[CH3:54])[C@@H:45]([CH2:56][O:57][C:58](=[O:60])[CH3:59])[O:44][C@H:43]1[C:61]1[CH:62]=[C:63]([C:18]2[CH:17]=[CH:16][C:15]([C@@H:14]3[C@@H:11]([CH2:10][CH2:9][C@@H:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[OH:37])[C:12](=[O:36])[N:13]3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:20][CH:19]=2)[CH:64]=[CH:65][CH:66]=1)(=[O:40])[CH3:39]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 59643929(3R,4S)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-phenyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]azetidin-2-oneHCID 59842194HCID 59842194, compound

Product 1

HCID 69257981HCID 69257981, compoundYield 18.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

(3R,4S)-3-[(3S)-3-(4-Fluorophenyl)-3-hydroxypropyl]-1-phenyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]azetidin-2-one (51.3 mg, 0.102 mmol) and (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-(3-bromophenyl)-D-glucitol (35.5 mg, 0.073 mmol) were dissolved in 2.0 mL of toluene and 0.25 mL of ethanol. 0.075 mL of 4 N potassium carbonate was added to the mixture followed by 5.0 mg of tetrakis(triphenylphosphine)palladium(0). The entire reaction was degassed three times with argon then heated to reflux for 4 h. The reaction was cooled to room temperature, diluted with 5 mL of water, and extracted with ethyl acetate (3×25 mL). The organic layers were combine, dried over sodium sulfate, filtered, concentrated and purified by column chromatography (12 g silica gel, 5% to 95% ethyl acetate-hexane) to afford 10.5 mg (13%) of (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-(4′-{(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl}biphenyl-3-yl)-D-glucitol as a clear oil.

Workup

  1. customThe entire reaction
  2. customwas degassed three times with argon
  3. temperaturethen heated
  4. temperatureto reflux for 4 h
  5. additiondiluted with 5 mL of water
  6. extractionextracted with ethyl acetate (3×25 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by column chromatography (12 g silica gel, 5% to 95% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0488ae6a126a4b99b826f67cca923ffe
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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