Potassium Phosphate, Tribasic → HCID 67115799, compound

HRID 1258847Notes

Reaction equation

HRID 1258847 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:16]([CH:19]2[C@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:23]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:20]2)=[CH:15][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][CH2:10][CH2:9][CH2:8]2.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:85]1(B(O)O)[CH2:87][CH2:86]1>C1(C)C=CC=CC=1.O>[CH:85]1([C:2]2[CH:18]=[CH:17][C:16]([CH:19]3[C@H:24]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@@H:23]([O:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C@H:22]([O:41][CH2:42][C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)[O:20]3)=[CH:15][C:3]=2[CH2:4][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[O:11][CH2:10][CH2:9][CH2:8]3)[CH2:87][CH2:86]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 67116170HCID 67116170, compound

Product 1

HCID 67115799HCID 67115799, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 6-[2-bromo-5-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzyl]-chroman (300 mg, 0.363 mmol) in toluene (1.6 mL) was added tricyclohexylphosphine (10 mg), potassium phosphate (346 mg, 1.63 mmol), water (81 μl), cyclopropylboronic acid (93 mg, 1.09 mmol). The reaction mixture was degassed for 45 min then palladium (II) acetate (4 mg) was added. After heating overnight at 100° C., the reaction mixture was cooled to room temperature and was filtered through celite. The celite was washed with an additional ethyl acetate (30 mL) and the organic layer of the filtrate was separated and washed with water (20 mL) followed by brine (20 mL), then dried over sodium sulfate and concentrated to give crude product which was further purified by column chromatography to furnish 6-[2-cyclopropyl-5-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzyl]-chroman (250 mg).

Workup

  1. customThe reaction mixture was degassed for 45 min
  2. additionpalladium (II) acetate (4 mg) was added
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationwas filtered through celite
  5. washThe celite was washed with an additional ethyl acetate (30 mL)
  6. customthe organic layer of the filtrate was separated
  7. washwashed with water (20 mL)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customto give crude product which
  11. customwas further purified by column chromatography

Sources & evidence

ORD record
ord-dff548ae0a944474ac6fec8623e06ac2
Source dataset
uspto-grants-2013_06
Patent number
US08466114B2

Reaction notes

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