1-Bromo-3-chloropropane → HCID 57281530, compound

HRID 373511Notes

Reaction equation

HRID 373511 reaction equation
[CH2:1]([NH:3][C:4]([C@@H:6]1[CH2:21][C@@:14]2([C:18](=[O:19])[NH:17][C:16](=[O:20])[NH:15]2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:22])[CH:12]=2)[O:7]1)=[O:5])[CH3:2].Br[CH2:24][CH2:25][CH2:26][Cl:27].[H-].[Na+]>CN(C)C=O.O>[CH2:1]([NH:3][C:4]([C@@H:6]1[CH2:21][C@@:14]2([C:18](=[O:19])[N:17]([CH2:24][CH2:25][CH2:26][Cl:27])[C:16](=[O:20])[NH:15]2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:22])[CH:12]=2)[O:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 57296558HCID 57296558, compound

Product 1

HCID 57281530HCID 57281530, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 962WaterSolvent

Procedure

To a solution of (2S,4S)-N-ethyl-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide (21.0 g, 68.4 mmol) in N,N-dimethylformamide (100 ml, 1.29 mmol) was added 1-bromo-3-chloropropane (21.5 g, 137 mmol). After adding 60% NaH (2.75 g, 68.8 mmol) over 30 minutes at 15°-20° C., the mixture was stirred for 15 hours at 15°-25° C. The reaction mixture was poured into iced water (500 ml), extracted with AcOEt (1000 ml×3), dried over MgSO4. The solvent was distilled off, the residue was chromatographed on silica gel, eluted with CH2Cl2 -CH2Cl2 /MeOH (9/1), and recrystallized from AcOEt to give the desired compound (19.3 g, 73.8%) as colorless prism crystals.

Workup

  1. extractionextracted with AcOEt (1000 ml×3)
  2. dry with materialdried over MgSO4
  3. distillationThe solvent was distilled off
  4. customthe residue was chromatographed on silica gel
  5. washeluted with CH2Cl2 -CH2Cl2 /MeOH (9/1)
  6. customrecrystallized from AcOEt

Sources & evidence

ORD record
ord-3844d0e118f540a697b704170096c007
Source dataset
uspto-grants-1992_11
Patent number
US05164391

Reaction notes

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