L-Tryptophan → (S)-3-(1H-Indol-3-yl)-2-(4-phenyl-butyrylamino)-propionic acid

HRID 1362579Notes

Reaction equation

HRID 1362579 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([O-])(O)=O.[Na+].O=C1CCC(=O)N1[O:28][C:29](=O)[CH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(#N)C>O>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][C@H:2]([NH:1][C:29](=[O:28])[CH2:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:13]([OH:15])=[O:14])=[CH:5]1

Participants

6

Reactant 4

HCID 6305L-TryptophanHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 139371181-[(4-Phenylbutanoyl)oxy]pyrrolidine-2,5-dione

Product 1

HCID 57796817(S)-3-(1H-Indol-3-yl)-2-(4-phenyl-butyrylamino)-propionic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(Method J15B) A suspension of L-tryptophan (2.040 g, 10 mmol) and NaHCO3 in water (15 ml) was treated with 4-phenyl-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester (15/95) (2.610 g, 10 mmol) followed by the addition of acetonitrile (ca. 15 ml) to get a clear solution. The reaction mixture was stirred at ambient temperature for 12 hours and acetonitrile was removed under reduced pressure. The residue was acidified with citric acid to pH 2 and extracted with ethyl acetate (100 ml). The organic layer was washed with water (2×20 ml), brine (20 ml), and dried (MgSO4). The solvents were evaporated to give the crude product 16/95 (3.160 g, 95%). 1H NMR (DMSO-d6, HMDSO) δ: 1.51-1.82 (2H, m); 1.96-2.24 (2H, m); 2.33-2.64 (2H, m); 2.80-3.38 (2H, m); 4.38-4.68 (1H, m); 6.82-7.66 (14H, m); 8.11 (1H, d, J=8.0 Hz); 10.87 (1H, m).

Workup

  1. customto get a clear solution
  2. customacetonitrile was removed under reduced pressure
  3. extractionextracted with ethyl acetate (100 ml)
  4. washThe organic layer was washed with water (2×20 ml), brine (20 ml)
  5. dry with materialdried (MgSO4)
  6. customThe solvents were evaporated

Sources & evidence

ORD record
ord-bc579aa79a2c43238fa08e9c0cc6e1ba
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

Loading…