Water → HCID 86675069, compound

HRID 1509344Notes

Reaction equation

HRID 1509344 reaction equation
[F:1][C:2]([F:13])([S:9](Cl)(=[O:11])=[O:10])[C:3]([F:8])([F:7])[CH2:4][CH2:5][OH:6].C(=O)([O-])O.[Na+].[OH:19][N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26].O>C(#N)C>[F:1][C:2]([F:13])([S:9]([O:19][N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26])(=[O:11])=[O:10])[C:3]([F:8])([F:7])[CH2:4][CH2:5][OH:6]

Participants

6

Reactant 4

HCID 962WaterHCID 80170N-HydroxysuccinimideHCID 516892Sodium BicarbonateHCID 86675070HCID 86675070, compound

Product 1

HCID 86675069HCID 86675069, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

In 100 mL of acetonitrile, 25 g of a liquid of 1,1,2,2-tetrafluoro-4-hydroxybutanesulfonyl chloride (purity: 90%, equivalent to 0.102 mol) was dissolved by stirring. The resulting solution was cooled to 0° C., admixed with 10.3 g (0.123 mol) of sodium hydrogencarbonate and 12.9 g (0.112 mol) of N-hydroxysuccinimide, and then, reacted at 0° C. for 24 hours. To the thus-obtained reaction solution, 125 mL of water was added. The reaction solution was subsequently extracted twice with 100 mL of ethyl acetate. The resulting organic layer was washed twice with 100 mL of water and subjected to concentration. With this, 23.4 g of the target compound was obtained as a pale yellow oily substance (yield: 56%, purity: 79%, pure content: 18.5 g).

Workup

  1. customreacted at 0° C. for 24 hours
  2. additionwas added
  3. extractionThe reaction solution was subsequently extracted twice with 100 mL of ethyl acetate
  4. washThe resulting organic layer was washed twice with 100 mL of water
  5. concentrationsubjected to concentration

Sources & evidence

ORD record
ord-80659d2d06104454811647e143c910fe
Source dataset
uspto-grants-2015_12
Patent number
US09221928B2

Reaction notes

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