Sodium Chloride → HCID 67460237, compound

HRID 554567Notes

Reaction equation

HRID 554567 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12](OS(C(F)(F)F)(=O)=O)=[CH:11][C@@H:10]1[CH2:39][O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+].[Br-].[CH2:50]([C:52]1[CH:67]=[CH:66][C:55]([CH2:56][C:57]2[CH:58]=[C:59](B(O)O)[CH:60]=[CH:61][CH:62]=2)=[CH:54][CH:53]=1)[CH3:51].[Cl-].[Na+]>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.O.O1CCOCC1.O>[CH2:50]([C:52]1[CH:67]=[CH:66][C:55]([CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([C:12]3[C@H:13]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C@@H:14]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C@H:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C@@H:10]([CH2:39][O:40][CH2:41][C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH:11]=3)[CH:58]=2)=[CH:54][CH:53]=1)[CH3:51]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 253877Potassium BromideHCID 59867294HCID 59867294, compoundHCID 67458641HCID 67458641, compound

Product 1

HCID 67460237HCID 67460237, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

In a nitrogen stream, dioxane-water (10:1)(12 mL) was added to a mixture of trifluoromethanesulfonic acid (3R,4R,5S,6R)-4,5,6-trisbenzyloxy-3-(benzyloxymethyl)cyclohex-1-enyl ester (656 mg, 0.981 mmol), K3PO3 (250 mg, 1.18 mmol), KBr (140 mg, 1.18 mmol), 3-(4-ethylbenzyl)phenylboronic acid (283 mg, 1.18 mmol) and Pd(PPh3)4 (56.6 mg, 0.049 mmol), and the reaction mixture was heated and stirred at a temperature of 100° C. to 105° C. for 26 hours. After cooling the reaction mixture, a saturated sodium chloride aqueous solution and water were added thereto. The resulting solution was extracted with ether, and the organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10 to 1:8) to obtain the title compound (510.0 mg, 73%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureAfter cooling the reaction mixture
  3. extractionThe resulting solution was extracted with ether
  4. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography [

Sources & evidence

ORD record
ord-1d7af6bd8a794694acd33d15edf02b9b
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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