Ammonium Chloride → HCID 66818022, compound

HRID 1755127Notes

Reaction equation

HRID 1755127 reaction equation
[C:1]([O:5][C:6](=[O:40])[N:7]([CH2:9][CH2:10][O:11][CH2:12][C@@H:13]1[C@H:17]([CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[O:16][C:15]([CH3:39])([CH3:38])[O:14]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl-].[NH4+]>C1COCC1>[C:1]([O:5][C:6](=[O:40])[N:7]([CH2:9][CH2:10][O:11][CH2:12][C@@H:13]1[C@H:17]([CH2:18][CH2:19][OH:20])[O:16][C:15]([CH3:39])([CH3:38])[O:14]1)[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 66817451HCID 66817451, compound

Product 1

HCID 66818022HCID 66818022, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-{(4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy}-ethyl)-methyl-carbamic acid tert-butyl ester (82.2 mg, 0.14 mmol) was dissolved in THF (0.19 mL). TBAF (1.0 M solution in THF, 0.19 mL, 0.19 mmol) was added at 0° C. and the mixture was stirred at room temperature for one hour in a nitrogen atmosphere. Saturated aqueous ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine, and then dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give {2-[(4R,5S)-5-(2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-ethyl}-methyl-carbamic acid tert-butyl ester (41.7 mg, 88%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d40dcd3e159146ac879627c569adfe32
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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