Thiophene → HCID 54393418, compound

HRID 1973493Notes

Reaction equation

HRID 1973493 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-dbe2ff71af2a4b0eaa3d30baccda4aa8
Source dataset
uspto-grants-1976_12
Patent number
US03997584

Reaction notes

Loading…