L-Tryptophan, ethyl ester → HCID 69419736, compound

HRID 1354379Notes

Reaction equation

HRID 1354379 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:13])C(O)=O)[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:14]([O:16][C:17](=[O:30])[C@H](CC1C2C(=CC=CC=2)NC=1)N)[CH3:15].[OH2:31].ON1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2N=N1.Cl.C[N:44]([CH3:53])[CH2:45][CH2:46][CH2:47][N:48]=[C:49]=NCC>CN(C)C=O.C(N(CC)CC)C>[CH2:14]([O:16][C:17](=[O:30])[CH:45]([NH:44][C:53](=[O:31])[CH2:13][CH2:9][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=1)[CH2:46][C:47]1[NH:48][C:49]2[C:38]([CH:37]=1)=[CH:39][CH:40]=[CH:41][CH:36]=2)[CH3:15]

Participants

7

Reactant 4

HCID 81996L-Tryptophan, ethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 20848968HCID 20848968, compound

Product 1

HCID 69419736HCID 69419736, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

3,4-dihydroxyphenyl propionic acid (5.8 g, 31.8 mmol), tryptophan ethyl ester (8.1 g, 34.9 mmol), 1-hydroxybenzotriazole hydrate (5.2 g, 38.5 mmol) were dissolved in dimethylformamide (60 mL). The resulting solution was then placed in a water bath at 0° C. and treated with triethylamine (14 mL), followed by stirring for 10 minutes. To the resulting mixture, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (7.3g, 38.5 mmol) was added. After removing the water bath, the mixture was stirred for 18 hours at room temperature. The reaction was diluted in water (200 mL), extracted with ethylacetate (EtOAc) (500 mL), dried over magnesium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography (column size: 45 mm×150 mm, silica gel 70-230 mesh, eluent: hexane/EtOAc (1/2)) to obtain 11.6 g of the title compound. The yield was 92%. The results of analyses of the compound are as follows:

Workup

  1. customThe resulting solution was then placed in a water bath at 0° C.
  2. customAfter removing the water bath
  3. stirringthe mixture was stirred for 18 hours at room temperature
  4. additionThe reaction was diluted in water (200 mL)
  5. extractionextracted with ethylacetate (EtOAc) (500 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. custompurified by silica gel column chromatography (column size: 45 mm×150 mm, silica gel 70-230 mesh, eluent: hexane/EtOAc (1/2))

Sources & evidence

ORD record
ord-9b4e7266510e410f96751d91f8a1a8ba
Source dataset
uspto-grants-2007_05
Patent number
US07223793B2

Reaction notes

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