Trifluoroacetic acid → HCID 53647970, compound

HRID 1462052Notes

Reaction equation

HRID 1462052 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH:8](O)[C:9]([OH:11])=[O:10])=[O:6])[CH:2]=[CH2:3].[S:13]1[CH:17]=[CH:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]1=2.FC(F)(F)C(O)=O.C(OCC)(=O)C>O>[CH2:1]([O:4][C:5]([N:7]([C:16]1[C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[S:13][CH:17]=1)[CH2:8][C:9]([OH:11])=[O:10])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7221Benzo(B)ThiopheneHCID 8857Ethyl AcetateHCID 13318579HCID 13318579, compound

Product 1

HCID 53647970HCID 53647970, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.15 g. (29.4 mM) of DL N-allyloxycarbonyl-α-hydroxyglycine and 3.95 g. (29.4 mM) of benzo[b]thiophene in 40 ml. of trifluoroacetic acid was stirred at 22.5° C. for eighteen hours. The reaction mixture was then concentrated by evaporation under reduced pressure to give an oil, and the oil was dissolved in a mixture of 100 ml. of ethyl acetate and 100 ml. of water. The organic layer was separated, and the aqueous layer was extracted twice more with 50 ml. portions of fresh ethyl acetate. The organic extracts were combined, washed with water, and then extracted twice with 100 ml. portions of 10% aqueous sodium bicarbonate. The aqueous extracts were combined, added to 100 ml. of fresh ethyl acetate, and acidified to pH 2.0 by the addition of conc. hydrochloric acid. The organic layer was separated and the aqueous acid layer was extracted with two 50 ml. portions of fresh ethyl acetate. The organic portions were combined, dried, and the solvent was removed by evaporation to provide 7.55 g. (88% yield) of N-allyloxycarbonyl-(3-benzothienyl)glycine.

Workup

  1. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  2. customto give an oil
  3. dissolutionthe oil was dissolved in a mixture of 100 ml
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice more with 50 ml
  6. washwashed with water
  7. extractionextracted twice with 100 ml
  8. additionadded to 100 ml
  9. additionof fresh ethyl acetate, and acidified to pH 2.0 by the addition of conc. hydrochloric acid
  10. customThe organic layer was separated
  11. extractionthe aqueous acid layer was extracted with two 50 ml
  12. customdried
  13. customthe solvent was removed by evaporation
  14. customto provide 7.55 g

Sources & evidence

ORD record
ord-275d06662cf8468ebbc18575da29140c
Source dataset
uspto-grants-1984_07
Patent number
US04458085

Reaction notes

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