2-Dimethylaminopyridine → {6-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-2,3,4,5-tetrahydroxy-hexyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 2075644Notes

Reaction equation

HRID 2075644 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:29])[NH:17][CH2:18][CH:19]([OH:28])[CH:20]([OH:27])[CH:21]([OH:26])[CH:22]([OH:25])[CH2:23][OH:24])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:30][O:31][C:32]1[CH:53]=[CH:52][C:35]([C:36](Cl)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)=[CH:34][CH:33]=1.CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:29])[NH:17][CH2:18][CH:19]([OH:28])[CH:20]([OH:27])[CH:21]([OH:26])[CH:22]([OH:25])[CH2:23][O:24][C:36]([C:35]3[CH:52]=[CH:53][C:32]([O:31][CH3:30])=[CH:33][CH:34]=3)([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 23132532(2,3,4,5,6-pentahydroxy-hexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 58687725{6-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-2,3,4,5-tetrahydroxy-hexyl}-carbamic acid 9H-fluoren-9-ylmethyl esterYield 57.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Compound 35 (5.0 g, 12.4 mmol) was dissolved in 100 ml of pyridine and azeotropically boiled. After this operation was conducted two times, the product was dissolved in 100 ml of dry pyridine and cooled with ice in a nitrogen stream. 4,4′-Dimethoxytrityl chloride (5.0 g, 14.9 mmol) and dimethylaminopyridine (1.5 g, 12.4 mmol) were added, the temperature was gradually increased from under ice cooling to room temperature, and this was followed by stirring at room temperature for 17 hours. After the pyridine was evaporated under reduced pressure, the residue was diluted with 500 ml of ethyl acetate. After water was added, the organic phase was separated, after which the water phase was again extracted with ethyl acetate. The ethyl acetate phase was washed with saturated brine, after which it was dried with anhydrous magnesium sulfate. After concentration under reduced pressure, the concentrate was purified by silica gel column chromatography (CHCl3:MeOH=10:1) to yield the desired compound (Compound 36: 5.06 g) at a percent yield of 57.9%.

Workup

  1. temperaturecooled with ice in a nitrogen stream
  2. customAfter the pyridine was evaporated under reduced pressure
  3. additionthe residue was diluted with 500 ml of ethyl acetate
  4. additionAfter water was added
  5. customthe organic phase was separated
  6. extractionafter which the water phase was again extracted with ethyl acetate
  7. washThe ethyl acetate phase was washed with saturated brine
  8. dry with materialafter which it was dried with anhydrous magnesium sulfate
  9. concentrationAfter concentration under reduced pressure
  10. customthe concentrate was purified by silica gel column chromatography (CHCl3:MeOH=10:1)

Sources & evidence

ORD record
ord-2ad30882265e43eba8d8f36a26a88b24
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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