Sodium Bicarbonate → HCID 68814490, compound

HRID 732486Notes

Reaction equation

HRID 732486 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 1.0 (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-40279891271f43c0a8a2f201496a3d98
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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