Anisole → HCID 14696302, compound

HRID 1200142Notes

Reaction equation

HRID 1200142 reaction equation
[CH3:1][C:2]([NH:10][C:11](=[O:36])[C@@H:12]([NH:28]C(OC(C)(C)C)=O)[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH3:9][C:2]([NH:10][C:11](=[O:36])[C@@H:12]([NH2:28])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])([CH3:1])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 14696300HCID 14696300, compound

Product 1

HCID 14696302HCID 14696302, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To 2.18 g of (2S)-N-(α,α-dimethylbenzyl)-2-(t-butoxycarbonylamino)-6-benzyloxycarbonylaminohexanamide (prepared as described in Preparation 8) were added 0.47 g of anisole and 10 ml of trifluoroacetic acid, and the solution was stirred for 30 minutes at room temperature. At the end of this time, the excess trifluoroacetic acid was distilled off under reduced pressure. A 5% w/v aqueous solution of sodium bicarbonate was added to the residue, and the mixture was neutralized and then extracted with ethyl acetate. The organic layer was extracted with a 10% w/v aqueous solution of citric acid. The aqueous extract was separated and neutralized with a 5% w/v aqueous solution of sodium bicarbonate and then extracted again with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, 1.01 g of the title compound was obtained as an amorphous material.

Workup

  1. distillationAt the end of this time, the excess trifluoroacetic acid was distilled off under reduced pressure
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate
  4. extractionThe organic layer was extracted with a 10% w/v aqueous solution of citric acid
  5. extractionThe aqueous extract
  6. customwas separated
  7. extractionextracted again with ethyl acetate
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-f15d5793d6b547e3be5f227d30196f26
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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