Water → HCID 117700856, compound

HRID 873534Notes

Reaction equation

HRID 873534 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[N:13]=[C:12]([N:14]2[CH2:22][CH2:21][CH2:20][C@@H:15]2[C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:10][CH:9]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][C:26]=1[CH:34]1[C:47]2[C:46](=[O:48])[CH2:45][C:44]([CH3:50])([CH3:49])[CH2:43][C:42]=2[O:41][C:40]2[CH2:39][C:38]([CH3:52])([CH3:51])[CH2:37][C:36](=[O:53])[C:35]1=2.O>C(COC)OC.O.C(OCC)(=O)C>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:8]2[N:13]=[C:12]([N:14]3[CH2:22][CH2:21][CH2:20][C@@H:15]3[C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:10][CH:9]=2)=[CH:27][C:26]=1[CH:34]1[C:35]2[C:36](=[O:53])[CH2:37][C:38]([CH3:51])([CH3:52])[CH2:39][C:40]=2[O:41][C:42]2[CH2:43][C:44]([CH3:50])([CH3:49])[CH2:45][C:46](=[O:48])[C:47]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 117700521HCID 117700521, compoundHCID 131732562[4-Methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]boronic acid

Product 1

HCID 117700856HCID 117700856, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Sodium carbonate (238 mg, 2.24 mmol) and tetrakistriphenylphosphine palladium(0) (86.3 mg, 74.7μμmol) were added to a solution of the methyl 1-(6-bromopyridin-2-yl)-D-prolinate (213 mg, 747 μmol) obtained in Example 15-1 and the [4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]boronic acid (317 mg, 747 μmol) obtained in Example 1-1 in dimethoxyethane/water (3:1, v/v) (4 mL) at room temperature. The mixture thus obtained was stirred at 80° C. for 4 hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate three times. The organic layer thus obtained was dried over anhydrous magnesium sulfate, and the solvent was then distilled away under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=8:2 to 1:3, v/v) to obtain the title compound (190 mg, yield: 44%).

Workup

  1. customat room temperature
  2. customThe mixture thus obtained
  3. extractionthe mixed solution was then extracted with ethyl acetate three times
  4. customThe organic layer thus obtained
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationthe solvent was then distilled away under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-a9832719f4c6439ea89bdadd58fb6962
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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