Potassium Phosphate, Tribasic → HCID 86691702, compound

HRID 1022472Notes

Reaction equation

HRID 1022472 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([C:15]2[CH:20]=[CH:19][C:18](Br)=[C:17]([CH2:22][C:23]3[CH:32]=[CH:31][C:26]4[O:27][CH2:28][CH2:29][O:30][C:25]=4[CH:24]=3)[CH:16]=2)[O:8][CH:7]([O:33][CH3:34])[C@H:6]1[O:35][C:36](=[O:38])[CH3:37])(=[O:3])[CH3:2].[CH:39]1(P(C2CCCCC2)C2CCCCC2)CCCC[CH2:40]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(B(O)O)C>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([C:15]2[CH:20]=[CH:19][C:18]([CH2:39][CH3:40])=[C:17]([CH2:22][C:23]3[CH:32]=[CH:31][C:26]4[O:27][CH2:28][CH2:29][O:30][C:25]=4[CH:24]=3)[CH:16]=2)[O:8][CH:7]([O:33][CH3:34])[C@H:6]1[O:35][C:36](=[O:38])[CH3:37])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 521157Ethylboronic acidHCID 86691703HCID 86691703, compound

Product 1

HCID 86691702HCID 86691702, compoundYield 125.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Step-III: To a stirred solution of acetic acid (3S,4R,5S,6S)-4,5-diacetoxy-6-[4-bromo-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-2-methoxy-tetrahydro-pyran-3-yl ester (700 mg, 1.18 mmol) in toluene (11 ml) was added tricyclohexylphosphine (132 mg, 0.47 mmol), a solution of potassium phosphate tribasic (1.0 g, 4.72 mmol) in water (1 ml), ethylboronic acid (262 mg, 3.54 mmol). The reaction mixture was degassed for 40 min then added palladium (II) acetate (39 mg, 0.18 mmol). Reaction mixture was stirred at 90° C. for overnight. Reaction mixture was cooled to room temperature and was filtered through celite bed, washed with ethyl acetate (10 ml). Organic layer was washed with water (15 ml) followed by brine (15 ml), dried over sodium sulfate, concentrated and purified by column chromatography to give 320 mg of acetic acid (3S,4R,5S,6S)-4,5-diacetoxy-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-2-methoxy-tetrahydro-pyran-3-yl ester as white solid.

Workup

  1. customThe reaction mixture was degassed for 40 min
  2. customReaction mixture
  3. customReaction mixture
  4. temperaturewas cooled to room temperature
  5. filtrationwas filtered through celite bed
  6. washwashed with ethyl acetate (10 ml)
  7. washOrganic layer was washed with water (15 ml)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-9e2e4451da0d4184b3867647c4eb72b4
Source dataset
uspto-grants-2014_05
Patent number
US08722633B2

Reaction notes

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