Anisole → HCID 18944016, compound

HRID 400304Notes

Reaction equation

HRID 400304 reaction equation
[CH2:1]([C:3]1[N:7](CCC)[N:6]=[C:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[S:24]([NH:27]C(C)(C)C)(=[O:26])=[O:25])=[CH:14][CH:13]=2)[C:4]=1[C:32]([O:34][CH3:35])=[O:33])[CH3:2].[C:36]1(OC)[CH:41]=CC=C[CH:37]=1.CCOC(C)=O>FC(F)(F)C(O)=O>[NH2:27][S:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:5]2[N:6]([CH2:37][CH2:36][CH3:41])[N:7]=[C:3]([CH2:1][CH3:2])[C:4]=2[C:32]([O:34][CH3:35])=[O:33])=[CH:13][CH:14]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 8857Ethyl AcetateHCID 18944048HCID 18944048, compound

Product 1

HCID 18944016HCID 18944016, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of the compound obtained in example 43 (2.65 g, 5.3 mmol) in trifluoroacetic acid (58 mL) was added anisole (1 mL) and the mixture stirred under an argon atmosphere for 18 h. The solvent was concentrated and the residue purified by chromatography on silica-gel (hexane-EtOAc mixtures) to give a 1:1 mixture of regioisomers, from which the title compound was obtained as a white solid by recrystallization from EtOAc (1.34 g, 57%).

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue purified by chromatography on silica-gel (hexane-EtOAc mixtures)
  3. customto give
  4. additiona 1:1 mixture of regioisomers

Sources & evidence

ORD record
ord-975b9f50f97c4bfe9ba043ce9c6f8936
Source dataset
uspto-grants-1998_10
Patent number
US05827863

Reaction notes

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