Sodium Bicarbonate → HCID 58542377, compound

HRID 1951917Notes

Reaction equation

HRID 1951917 reaction equation
[CH2:1]([N:8]1[CH2:15][C:12]2([CH2:14][CH2:13]2)[N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][C@@H:9]1[CH2:23]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCN(S(F)(F)[F:35])CCOC.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([N:8]1[CH2:15][C:12]2([CH2:14][CH2:13]2)[N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][C@@H:9]1[CH2:23][F:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 58542352HCID 58542352, compound

Product 1

HCID 58542377HCID 58542377, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A dichloromethane (8 ml) solution of the compound (360 mg, 1.08 mmol) obtained in Step 6 above was cooled to −78° C. Subsequently, bis(2-methoxyethyl)aminosulfur trifluoride (0.26 ml, 1.41 mmol) was added dropwise and the resulting mixture was gradually heated and stirred for 20 hours. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate solution, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, then the drying agent was removed by filtration and the solvent was concentrated under reduced pressure. The residue obtained was purified by silica gel chromatography [ethyl acetate:n-hexane=1:10 (v/v)] to give the title compound (325 mg, 90%) as a colorless oil.

Workup

  1. temperaturethe resulting mixture was gradually heated
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe drying agent was removed by filtration
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by silica gel chromatography [ethyl acetate:n-hexane=1:10 (v/v)]

Sources & evidence

ORD record
ord-6946a899a1e94e039998ccd8bbee96b3
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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