1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → 6-O-(4,4'-dimethoxytrityl)-2-deoxy-2(thymin-1yl]-3-O-(2-fluoroethyl)D-altro-hexitol

HRID 43299Notes

Reaction equation

HRID 43299 reaction equation
[N:1]1([C@@H:10]([C@@H:13]([C@@H:18]([C@@H:20]([CH2:22][OH:23])[OH:21])[OH:19])[O:14][CH2:15][CH2:16][F:17])[CH2:11][OH:12])[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH3:24][O:25][C:26]1[CH:47]=[CH:46][C:29]([C:30](Cl)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[CH:28][CH:27]=1>>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([C:30]([O:23][CH2:22][C@@H:20]([OH:21])[C@@H:18]([OH:19])[C@@H:13]([O:14][CH2:15][CH2:16][F:17])[C@H:10]([N:1]2[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]2=[O:3])[CH2:11][OH:12])([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:29]2[CH:46]=[CH:47][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 866614452-deoxy-2-(thymin-1yl)-3-O-(2-fluoroethyl)-D-altro-hexitol

Product 1

HCID 866614446-O-(4,4'-dimethoxytrityl)-2-deoxy-2(thymin-1yl]-3-O-(2-fluoroethyl)D-altro-hexitolYield 89%

Procedure

Compound 5 (4.07 g, 12.79 mmol) was mixed with 4,4′-dimethoxytrityl chloride (4.56 g, 13.46 mmol) and dried over P2O5 under reduced pressure. The residue was dissolved in anhydrous pyridine (43 mL) and stirred at room temperature for 6 hours under an atmosphere of argon. The mixture was quenched with methanol (3 mL). The reaction mixture was diluted with EtOAc (200 mL), washed with aqueous NaHCO3 (saturated, 300 mL) and brine (200 mL) then dried over Na2SO4, filtered and concentrated. The residue obtained was purified by silica gel column chromatography (eluted first with 70% EtOAc in hexanes and then increasing the polarity) to yield Compound 6 (7.1 g, 89%). ES MS m/z 643.2 [M+Na]+.

Workup

  1. dry with materialdried over P2O5 under reduced pressure
  2. dissolutionThe residue was dissolved in anhydrous pyridine (43 mL)
  3. customThe mixture was quenched with methanol (3 mL)
  4. additionThe reaction mixture was diluted with EtOAc (200 mL)
  5. washwashed with aqueous NaHCO3 (saturated, 300 mL) and brine (200 mL)
  6. dry with materialthen dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography (
  11. washeluted first with 70% EtOAc in hexanes
  12. temperatureincreasing the polarity)

Sources & evidence

ORD record
ord-99749642d8f449818cfcf864ee94ddd9
Source dataset
uspto-grants-2013_09
Patent number
US08536320B2

Reaction notes

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