Ethanol, 1-ethoxy-2,2,2-trifluoro- → HCID 117903710, compound

HRID 631815Notes

Reaction equation

HRID 631815 reaction equation
C(OC([N:8]([S:26]([CH2:29]P(OCC)(OCC)=O)(=[O:28])=[O:27])[CH2:9][CH2:10][N:11]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O)(C)(C)C.[H-].[Na+].C(O[CH:43](O)[C:44]([F:47])([F:46])[F:45])C>C1COCC1>[CH3:25][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([N:11]([CH2:10][CH2:9][NH:8][S:26](/[CH:29]=[CH:43]/[C:44]([F:47])([F:46])[F:45])(=[O:27])=[O:28])[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH:24]=1

Participants

5

Reactant 3

HCID 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-HCID 24758Sodium hydrideHCID 89825809HCID 89825809, compound

Product 1

HCID 117903710HCID 117903710, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-[2-(tert-butoxycarbonyl(diethoxyphosphorylmethyl-sulfonyl)amino)-ethyl]-N-(4-methyl-2-pyridyl)carbamate (344 mg, 0.608 mmol) in anhydrous THF (30 ml) were added molsieve (4A) and sodium hydride (42.5 mg, 1.063 mmol, 60%) under nitrogen and the mixture was stirred at room temperature for 10 minutes. The mixture was cooled to 0° C. and 1-ethoxy-2,2,2-trifluoro-ethanol (220 mg, 1.525 mmol, 180 μl) was added. Stirring was continued for 30 minutes at 0° C. and overnight at room temperature. The mixture was filtered through kieselguhr and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica, gradient of 0 to 100% heptane in ethyl acetate) to yield 98 mg of a colourless oil (0.239 mmol, 39%) MS(ESI) m/z=410.1 [M+1]+.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringStirring
  3. waitwas continued for 30 minutes at 0° C. and overnight at room temperature
  4. filtrationThe mixture was filtered through kieselguhr
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica, gradient of 0 to 100% heptane in ethyl acetate)

Sources & evidence

ORD record
ord-7052c8fd575e49179075977bf93bf3ba
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

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