Water → N-[(Perfluorobutyl)sulfonyl]-N-propylglycine

HRID 1158607Notes

Reaction equation

HRID 1158607 reaction equation
[C:1]([S:14]([N:17]([CH2:21][C:22]([O:24]CC)=[O:23])[CH2:18][CH2:19][CH3:20])(=[O:16])=[O:15])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].[OH-].[K+].O>C(O)(C)C>[C:1]([S:14]([N:17]([CH2:21][C:22]([OH:24])=[O:23])[CH2:18][CH2:19][CH3:20])(=[O:15])=[O:16])([C:4]([C:7]([C:10]([F:11])([F:13])[F:12])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 131726678HCID 131726678, compound

Product 1

HCID 86068660N-[(Perfluorobutyl)sulfonyl]-N-propylglycineYield 65.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
56 °C

Procedure

A one-liter flask fitted with a thermocouple, addition tunnel, heating mantle, reflux condenser and overhead stirrer was charged with C4F9SO2NH(C3H7) (120.0 g; 0.352 mole), and sodium carbonate (39.0 g). The mixture was heated to 93° C. and ethyl bromoacetate (62.0 g; 0.371 mole) was slowly added over a period of 4 hours, and then the ensuing mixture was allowed to stir overnight at 93° C. To this mixture was added water (120.0 mL) and the temperature was 56° C., at which point sulfuric acid (23.8 g; concentrated) at a rate to keep the temperature below 100° C. Two phases formed and the bottom layer was recovered and washed with water (150 mL). This crude material was distilled (95-121° C.; 4.0 mm Hg) to yield C4F9SO2N(C3H7)CH2CO2C2H5 (132.0 g). A one-liter flask fitted with a thermocouple, addition funnel, heating mantle, reflux condenser and overhead stirrer was charged with C4F9SO2N(C3H7)CH2CO2C2H5 (116.0 g; 0.27 mole) KOH (20.0 g; 0.303 mole) water (60 mL) and isopropanol (60.0 g). The mixture was heated at reflux for 2 hours, and a Dean-Stark trap was added. As isopropanol was removed from the trap, an equivalent amount of water was added to the reaction mixture. When the reaction mixture reached 101° C. water (25 mL) was added and the mixture was cooled to 56° C.; upon addition of sulfuric acid (31.0 g; concentrated) the temperature increased to 78° C. and two phases appeared. The bottom phase was separated and distilled (136-142° C.; 4.0-5.4 mm Hg) to yield a white solid, C4F9SO2N(C3H7)CH2CO2H (71.0 g).

Workup

  1. customA one-liter flask fitted with a thermocouple, addition funnel
  2. temperatureheating mantle
  3. temperaturereflux condenser and overhead stirrer
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 2 hours
  6. additiona Dean-Stark trap was added
  7. customAs isopropanol was removed from the trap
  8. additionan equivalent amount of water was added to the reaction mixture
  9. customreached 101° C.
  10. additionwas added
  11. additionupon addition of sulfuric acid (31.0 g; concentrated) the temperature
  12. temperatureincreased to 78° C.
  13. customThe bottom phase was separated
  14. distillationdistilled (136-142° C.; 4.0-5.4 mm Hg)

Sources & evidence

ORD record
ord-1db9530e824547359b492fee1aad5b1f
Source dataset
uspto-grants-2010_10
Patent number
US07811978B2

Reaction notes

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