Water → HCID 86655528, compound

HRID 1746590Notes

Reaction equation

HRID 1746590 reaction equation
O.[CH3:2][N:3]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:5]([CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])=[CH:4]1.C(=O)([O-])O.[Na+].[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]=[CH:32][C:33](ON1C(=O)CCC1=O)=[O:34])#[N:24]>O1CCOCC1>[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]=[CH:32][C:33]([NH:8][C@H:7]([C:9]([OH:11])=[O:10])[CH2:6][C:5]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]([CH3:2])[CH:4]=1)=[O:34])#[N:24]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 6761591-Methyl-L-tryptophanHCID 86655529HCID 86655529, compound

Product 1

HCID 86655528HCID 86655528, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To water (60 mL)-dioxane (60 mL) suspension of 1-methyl-L-tryptophan (2.1 g) was added sodium hydrogencarbonate (0.8 g) at 0° C., and the mixture was stirred for 30 minutes at room temperature. Dioxane (80 mL) solution of 2,5-dioxopyrrolidin-1-yl 3-(2-cyanophenyl)acrylate (2.5 g, 9.2 mmol) was added dropwise to the reaction mixture at 0° C., and the mixture was stirred for 15 hours at room temperature. The reaction mixture was concentrated to a ⅓ volume under a reduced pressure, water was added thereto, and the mixture was washed with diethyl ether. The aqueous layer was made acidic with a 10% aqueous citric acid solution, and thereafter extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, and thereafter dried over anhydrous sodium sulfate. The solvent was distilled off under a reduced pressure, to give the captioned compound (0.96 g, 27%) as an amorphous solid product.

Workup

  1. stirringthe mixture was stirred for 15 hours at room temperature
  2. concentrationThe reaction mixture was concentrated to a ⅓ volume under a reduced pressure, water
  3. additionwas added
  4. washthe mixture was washed with diethyl ether
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-8c937d690d4e4b2aaf40ae53d9f0b66c
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

Loading…