Thiophene → HCID 54393418, compound

HRID 2420020Notes

Reaction equation

HRID 2420020 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 ad 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-6a745bf1a6e94af19c6ac68a860d14b7
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

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