Trifluoroacetic acid → S-Acetylthioglycolic acid NHS ester

HRID 2213026Notes

Reaction equation

HRID 2213026 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH2:9][C:10]1([CH2:23][C:24]([CH3:26])=[CH2:25])[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]1>ClCCl>[CH3:25][C:24]1([CH3:26])[CH2:23][C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:9][O:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69557602HCID 69557602, compound

Product 1

HCID 21955272S-Acetylthioglycolic acid NHS esterYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 mL) was added to a solution of 1-(1,1-dimethylethyl) 4-(hydroxymethyl)-4-(2-methyl-2-propenyl)-1-piperidinecarboxylate (Description 90, 1.14 g, 4.2 mmol) in dichloromethane (4 mL) and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and water (40 mL) was added. The pH was adjusted to 12 with aqueous sodium hydroxide (4M) and the mixture was extracted with ethyl acetate (4×40 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was dissolved in ethanol (10 mL) and ethereal hydrogen chloride (1M, 10 mL) was added. The solvent was evaporated under reduced pressure and the residue was triturated with ethyl acetate (15 mL). The solid was collected and dried in vacuo to give the title compound as a colorless solid (483 mg, 56%). m/z (ES+) 170 (M+1).

Workup

  1. customThe solvent was evaporated under reduced pressure and water (40 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (4×40 mL)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in ethanol (10 mL)
  7. additionethereal hydrogen chloride (1M, 10 mL) was added
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was triturated with ethyl acetate (15 mL)
  10. customThe solid was collected
  11. customdried in vacuo

Sources & evidence

ORD record
ord-e8e351e382bf46c6b1d7893c47242834
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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