L-Tryptophan → 2,5,7-Tri-tert-butyl-L-tryptophan

HRID 516193Notes

Reaction equation

HRID 516193 reaction equation
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[C:16](O)([CH3:19])([CH3:18])[CH3:17]>FC(F)(F)C(O)=O>[C:16]([C:5]1[NH:6][C:7]2[C:12](=[CH:11][C:10]([C:4]([CH3:12])([CH3:5])[CH3:3])=[CH:9][C:8]=2[C:16]([CH3:19])([CH3:18])[CH3:17])[C:4]=1[CH2:3][C@@H:2]([C:13]([OH:15])=[O:14])[NH2:1])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6305L-TryptophanHCID 6386tert-Butanol

Product 1

HCID 131749612,5,7-Tri-tert-butyl-L-tryptophanYield 85%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tryptophan (4.00 g, 19.59 mmol), trifluoroacetic acid 98% (60 ml) and tert-butanol (15.54 g, 209.66 mmol) were mixed. The reaction mixture was stirred at room temperature for 48 hours. The trifluoroacetic acid was evaporated. The residue was suspended in 40 ml distilled water, and the pH adjusted to neutral with addition of sodium hydrogen carbonate. The crude product was obtained by filtration. Crystallisation from 50% ethanol afforded the product as a white powder (85-90% pure).

Workup

  1. customThe trifluoroacetic acid was evaporated
  2. distillationdistilled water
  3. additionneutral with addition of sodium hydrogen carbonate
  4. customThe crude product was obtained by filtration
  5. customCrystallisation from 50% ethanol

Sources & evidence

ORD record
ord-fe421669ffe843f484e230b11b0d6b4d
Source dataset
uspto-grants-2015_08
Patent number
US09109048B2

Reaction notes

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