Potassium Phosphate, Tribasic → HCID 86691700, compound

HRID 1022469Notes

Reaction equation

HRID 1022469 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22](Br)=[C:21]([CH2:26][C:27]3[CH:36]=[CH:35][C:30]4[O:31][CH2:32][CH2:33][O:34][C:29]=4[CH:28]=3)[CH:20]=2)[O:7][CH:6]1[O:37][C:38](=[O:40])[CH3:39])(=[O:3])[CH3:2].C1(P([CH:54]2[CH2:59][CH2:58]CCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(B(O)O)CC1>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]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([CH:58]3[CH2:59][CH2:54]3)=[C:21]([CH2:26][C:27]3[CH:36]=[CH:35][C:30]4[O:31][CH2:32][CH2:33][O:34][C:29]=4[CH:28]=3)[CH:20]=2)[O:7][CH:6]1[O:37][C:38](=[O:40])[CH3:39])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 86691699HCID 86691699, compound

Product 1

HCID 86691700HCID 86691700, compoundYield 181.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Step-IX: To a stirred solution of acetic acid (3S,4R,5S,6S)-3,4,5-triacetoxy-6-[4-bromo-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-tetrahydro-pyran-2-yl ester (2.75 g, 4.4 mmol) in toluene (25 ml) was added tricyclohexylphosphine (495 mg, 1.8 mmol), a solution of potassium phosphate tribasic (3.75 g, 1.8 mmol) in water (5 ml), cyclopropylboronic acid (1.14 g, 13.2 mmol). The reaction mixture was degassed for 45 min then added palladium (II) acetate (148 mg, 0.7 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 (25 ml). Organic layer was washed with water (25 ml) followed by brine (25 ml), dried over sodium sulfate, concentrated and purified by column chromatography to give 1.9 g of acetic acid (3S,4R,5S,6S)-3,4,5-triacetoxy-6-[4-cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-tetrahydro-pyran-2-yl ester. MS (ES) m/z 600.3 (M+18).

Workup

  1. customThe reaction mixture was degassed for 45 min
  2. customReaction mixture
  3. customReaction mixture
  4. temperaturewas cooled to room temperature
  5. filtrationwas filtered through celite bed
  6. washwashed with ethyl acetate (25 ml)
  7. washOrganic layer was washed with water (25 ml)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-72371ea7333e470180a84fca2751758a
Source dataset
uspto-grants-2014_05
Patent number
US08722633B2

Reaction notes

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