Mannitol → HCID 10556358, compound

HRID 1401060Notes

Reaction equation

HRID 1401060 reaction equation
[CH2:1]([OH:12])[C@H:2]([C@H:4]([C@@H:6]([C@@H:8]([CH2:10][OH:11])[OH:9])[OH:7])[OH:5])[OH:3].CO[C:15]1[CH:34]=[CH:33][C:18]([C:19](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=1.C(Cl)Cl>N1C=CC=CC=1>[C:19]([O:11][CH2:10][C@H:8]([C@H:6]([C@@H:4]([C@@H:2]([CH2:1][O:12][C:19]([C:18]1[CH:33]=[CH:34][CH:15]=[CH:16][CH:17]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[OH:3])[OH:5])[OH:7])[OH:9])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:18]1[CH:33]=[CH:34][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6251MannitolHCID 6344DichloromethaneHCID 84462p-(Chlorodiphenylmethyl)anisole

Product 1

HCID 10556358HCID 10556358, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a flask containing 1 g of D-mannitol (5.49 mmols) and 3.73 g of 4-methoxytrityl chloride (12.07 mmols) were added 26.7 mL anhydrous DCM. Once all material dissolved 13.35 mL of pyridine was added. The reaction mixture was refluxed for 5 hours then allowed to cool to RT overnight. The reaction was quenched with 25 mL of water then extracted 3 times with 7 mL of DCM buffered with 0.1% triethylamine. The organic fractions were combined then washed 3 times with 7 mL of brine. The DCM layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was dissolved in a minimum amount of DCM and subjected to silica gel column chromatographic purification (EtOAc/hexanes) to obtain 3.2 g of the desired product (80% yield). 1H-NMR (500 MHz, CDCl3): δ 7.34 (m, 6H, aromatic), 7.24 (m, 24H, aromatic), 6.71 (m, 4H, aromatic), 3.83 (s, 1H, —OH), 3.72 (s, 6H, CH3), 3.687 (broad peak, 4H, CH2), 3.24 (m, 4H, —CH—), 2.88 (s, 1H, —OH), 2.62 (s, 1H, —OH). Mass spec analysis (MALDI-TOF): exact mass: 726.32, obtained: 749.86 [M+Na]+.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 5 hours
  3. customThe reaction was quenched with 25 mL of water
  4. extractionthen extracted 3 times with 7 mL of DCM
  5. washThe organic fractions were combined then washed 3 times with 7 mL of brine
  6. dry with materialThe DCM layers were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe resulting residue was dissolved in a minimum amount of DCM
  10. customsubjected to silica gel column chromatographic purification (EtOAc/hexanes)

Sources & evidence

ORD record
ord-941d7f9c17b142b587bd39fdd588908d
Source dataset
uspto-grants-2014_12
Patent number
US08907079B2

Reaction notes

Loading…