Sodium hydride → HCID 66817451, compound

HRID 1755126Notes

Reaction equation

HRID 1755126 reaction equation
[C:1]([O:5][C:6](=[O:12])[N:7]([CH2:9][CH2:10][OH:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:15]([Si:19]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[O:20][CH2:21][CH2:22][C@@H:23]1[O:27][C:26]([CH3:29])([CH3:28])[O:25][C@@H:24]1[CH2:30]OS(C(F)(F)F)(=O)=O)([CH3:18])([CH3:17])[CH3:16].[Cl-].[NH4+]>C1COCC1>[C:1]([O:5][C:6](=[O:12])[N:7]([CH2:9][CH2:10][O:11][CH2:30][C@@H:24]1[C@H:23]([CH2:22][CH2:21][O:20][Si:19]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[O:27][C:26]([CH3:28])([CH3:29])[O:25]1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 86672800HCID 86672800, compound

Product 1

HCID 66817451HCID 66817451, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(2-Hydroxy-ethyl)-methyl-carbamic acid tert-butyl ester (73.9 mg, 0.42 mmol) was dissolved in THF (1.15 mL). Sodium hydride (50%, 22.1 mg, 0.46 mmol) was added at 0° C. and the mixture was stirred at 0° C. for 10 minutes in a nitrogen atmosphere. Trifluoro-methanesulfonic acid (4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester was added to the reaction solution, and the mixture was stirred at room temperature for two hours 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, dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give (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, 38%).

Workup

  1. stirringthe mixture was stirred at room temperature for two hours in a nitrogen atmosphere
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-39f84212b92c42f6adf3bcf123b3662e
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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