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

HRID 2061332Notes

Reaction equation

HRID 2061332 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-tryptophan

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 affored 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

Sources & evidence

ORD record
ord-b5625f563a114693a20f5eb096d6ee09
Source dataset
uspto-grants-2012_10
Patent number
US08283315B2

Reaction notes

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