1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 10139659, compound

HRID 1265305Notes

Reaction equation

HRID 1265305 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:12][CH:10]1[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:35][CH2:36][N:37]1C(=O)C2=CC=CC=C2C1=O.O.NN>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[CH2:1]([O:8][C@@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:13]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:12][CH:10]1[O:11][CH2:35][CH2:36][NH2:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 109387022,3,5-Tri-O-benzyl-D-ribofuranose

Product 1

HCID 10139659HCID 10139659, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent3×

Conditions

Temperature
10 °C

Procedure

A mixture that consists of 42.1 g (100 mmol) of 2,3,5-tri-O-benzyl-ribofuranose, 3.40 g (10 mmol) of tetrabutylammonium hydrogen sulfate and 33.7 g (600 mmol) of fine-powder potassium hydroxide in 3050 ml of benzene is cooled to 10° C. At 10° C., 38.1 g (150 mmol) of N-(2-bromoethyl)-phthalimide, dissolved in 100 ml of benzene, is added in drops over 40 minutes while being stirred vigorously. It is stirred for three hours at 10° C. 300 ml of benzene is added, solid is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The filtrate residue is dissolved in 500 ml of ethanol, 25.03 g of hydrazine hydrate (500 mmol) is added, and it is refluxed for six hours. It is allowed to cool to 0° C., deposited precipitate is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The residue is dissolved in 400 ml of dichloromethane, and this solution is washed twice with 5% aqueous sodium hydroxide solution and then once with water (in each case 300 ml). The organic phase is evaporated to the dry state in a vacuum, and the residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol/triethylamine=20:2:0.1).

Workup

  1. additionis added in drops over 40 minutes
  2. stirringIt is stirred for three hours at 10° C
  3. filtrationsolid is filtered out
  4. customthe filtrate is evaporated to the dry state in a vacuum
  5. dissolutionThe filtrate residue is dissolved in 500 ml of ethanol
  6. temperatureit is refluxed for six hours
  7. temperatureto cool to 0° C.
  8. filtrationis filtered out
  9. customthe filtrate is evaporated to the dry state in a vacuum
  10. dissolutionThe residue is dissolved in 400 ml of dichloromethane
  11. washthis solution is washed twice with 5% aqueous sodium hydroxide solution
  12. customThe organic phase is evaporated to the dry state in a vacuum
  13. customthe residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol/triethylamine=20:2:0.1)

Sources & evidence

ORD record
ord-42c1bcf7b73a44c3a361c091455084e0
Source dataset
uspto-grants-2003_04
Patent number
US06545135B2

Reaction notes

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