Anisole → HCID 20312410, compound

HRID 2420008Notes

Reaction equation

HRID 2420008 reaction equation
[CH2:1]([O:5][C:6](=[O:20])[CH:7](OC(=O)C)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2][CH2:3][CH3:4].[C:21]1([O:27][CH3:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>B(F)(F)F.CCOCC.C(Cl)Cl>[CH2:1]([O:5][C:6](=[O:20])[CH:7]([C:24]1[CH:25]=[CH:26][C:21]([O:27][CH3:28])=[CH:22][CH:23]=1)[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 7519AnisoleHCID 20312395HCID 20312395, compound

Product 1

HCID 20312410HCID 20312410, compound

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 290 mg. (1 mmol.) of N-t-butoxycarbonyl-2-acetoxyglycine n-butyl ester, 0.5 ml. of anisole and 3 drops of boron trifluoride etherate in 5 ml. of methylene chloride was stirred at 25° for 4 hours. The solvent was removed and the residue was chromatographed on silica gel and eluted with 1:1 chloroform-hexane to give the title compound.

Workup

  1. customThe solvent was removed
  2. customthe residue was chromatographed on silica gel
  3. washeluted with 1:1 chloroform-hexane

Sources & evidence

ORD record
ord-6094deec65994f21a8748885a1119e83
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

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