Benzo(B)Thiophene → HCID 53647970, compound

HRID 2412407Notes

Reaction equation

HRID 2412407 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>[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

4

Reactant 2

HCID 7221Benzo(B)ThiopheneHCID 13318579HCID 13318579, compound

Product 1

HCID 53647970HCID 53647970, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

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 given 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. dissolutionthe oil was dissolved in a mixture of 100 ml of ethyl acetate and 100 ml of water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice more with 50 ml portions of fresh ethyl acetate
  5. washwashed with water
  6. extractionextracted twice with 100 ml portions of 10% aqueous sodium bicarbonate
  7. additionadded to 100 ml of fresh ethyl acetate
  8. additionacidified to pH 2.0 by the addition of conc. hydrochloric acid
  9. customThe organic layer was separated
  10. extractionthe aqueous acid layer was extracted with two 50 ml portions of fresh ethyl acetate
  11. customdried
  12. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-a73b9dc16ebe4aa58ef693c489089a0f
Source dataset
uspto-grants-1985_01
Patent number
US04492693

Reaction notes

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