Thiophene → HCID 54393418, compound

HRID 1731049Notes

Reaction equation

HRID 1731049 reaction equation
[CH2:1]([O:5][C:6](=[O:23])[CH:7](OC(=O)C)[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH2:2][CH2:3][CH3:4].[S:24]1[CH:28]=[CH:27][CH:26]=[CH:25]1>B(F)(F)F.CCOCC.C(Cl)Cl>[CH2:1]([O:5][C:6](=[O:23])[CH:7]([NH:8][C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[C:25]1[S:24][CH:28]=[CH:27][CH:26]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 8030ThiopheneHCID 20312421HCID 20312421, compound

Product 1

HCID 54393418HCID 54393418, compound

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.6 g. (5.0 mmol.) of N-benzyloxycarbonyl-2-acetoxyglycine n-butyl ester and 1.0 ml. of thiophene in 10 ml. of methylene chloride was treated with three drops of boron trifluoride etherate and left to stir at 25° for 16 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in methylene chloride and chromatographed on silica gel with methylene chloride containing increasing amounts of ethyl acetate to give the title compound, m.p. 37°.

Workup

  1. waitleft
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in methylene chloride
  4. customchromatographed on silica gel with methylene chloride containing
  5. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-3d58c7beb2e2485db099b3d0172ae516
Source dataset
uspto-grants-1976_11
Patent number
US03994954

Reaction notes

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