1-Bromo-3-chloropropane → HCID 57114724, compound

HRID 373512Notes

Reaction equation

HRID 373512 reaction equation
[CH2:1]([NH:5][C:6]([C@@H:8]1[CH2:23][C@@:16]2([C:20](=[O:21])[NH:19][C:18](=[O:22])[NH:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:24])[CH:14]=2)[O:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].Br[CH2:26][CH2:27][CH2:28][Cl:29].[H-].[Na+]>CN(C)C=O.O>[CH2:1]([NH:5][C:6]([C@@H:8]1[CH2:23][C@@:16]2([C:20](=[O:21])[N:19]([CH2:26][CH2:27][CH2:28][Cl:29])[C:18](=[O:22])[NH:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:24])[CH:14]=2)[O:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 57161498HCID 57161498, compound

Product 1

HCID 57114724HCID 57114724, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 962WaterSolvent

Procedure

To a solution of (2S,4S)-N-butyl-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide (25.0 g, 74.6 mmol) in N,N-dimethylformamide (125 ml, 1.62 mmol) was added 1-bromo-3-chloropropane (23.5 g, 149 mmol). After adding 60% NaH (3.00 g, 75.0 mmol) over 30 minutes at 15°-22° C., the mixture was stirred for 5 hours at 25°-28° 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 (24.7 g, 80.5%) 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-b237333a17204a88afb60e842ab9925c
Source dataset
uspto-grants-1992_11
Patent number
US05164391

Reaction notes

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