Sodium Bicarbonate → HCID 68814490, compound

HRID 1436629Notes

Reaction equation

HRID 1436629 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[CH2:14]([O:16][C:17](=[O:33])[C:18]1[CH:30]=[C:29]([CH2:31]O)[CH:28]=[C:20]([C:21]([N:23]([CH3:27])[CH2:24][CH2:25][CH3:26])=[O:22])[CH:19]=1)[CH3:15].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:14]([O:16][C:17](=[O:33])[C:18]1[CH:30]=[C:29]([CH2:31][F:11])[CH:28]=[C:20]([C:21]([N:23]([CH3:27])[CH2:24][CH2:25][CH3:26])=[O:22])[CH:19]=1)[CH3:15]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 688164795-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 68814490HCID 68814490, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Add bis(2-methoxyethyl) aminosulfur trifluoride (220 mg, 1.0 mmol) to a polypropylene tube (5 mL), seal, cool to −78° C., add a solution of 5-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (250 mg, 0.9 mmol) in dichloromethane (1 mL) in 0.2 mL increments. Stir at −78° C. for 3 h then at room temperature overnight. Pour the reaction into saturated aqueous sodium bicarbonate. Extract with dichloromethane, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes) to give the title compound (73 mg, 29%).

Workup

  1. customseal
  2. customat room temperature
  3. customovernight
  4. additionPour
  5. extractionExtract with dichloromethane
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-1f6479579f9b46adb9ed0708702855f1
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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