Benzyl chloroformate → HCID 140397781, compound

HRID 1417205Notes

Reaction equation

HRID 1417205 reaction equation
Cl.[Br:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[NH:15])[NH2:14])=[CH:9][CH:8]=1.[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(=O)([O-])[O-].[Na+].[Na+].O.C(Cl)Cl>[Br:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[NH:14])[NH:15][C:24]([O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:25])=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 10387Benzyl chloroformateHCID 22122301HCID 22122301, compound

Product 1

HCID 140397781HCID 140397781, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

In a mixed solvent of 175 ml of a saturated aqueous sodium carbonate solution, 90 ml of water and 350 ml of methylene chloride was dissolved 17.5 g of 1-bromo-3-(4-amidinophenoxy)propane hydrochloride, and 8.5 ml of benzyloxycarbonyl chloride was added thereto under ice-cooling. The resulting mixture was vigorously stirred at the same temperature for 30 minutes and then at room temperature for 4 hours, after which the organic layer was separated and the aqueous layer was extracted with 150 ml of methylene chloride. The combined organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. Hexane was added to the resulting residue and the crystals were collected by filtration and dried to obtain 19.6 g of 1-bromo-3-(4-benzyloxycarbonylamidinophenoxy)propane as colorless crystals.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. waitat room temperature for 4 hours
  4. customafter which the organic layer was separated
  5. extractionthe aqueous layer was extracted with 150 ml of methylene chloride
  6. washThe combined organic layer was washed with water
  7. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. additionHexane was added to the resulting residue
  11. filtrationthe crystals were collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-4de5259a5f7c4f9aa3e70a0a17ed1c41
Source dataset
uspto-grants-1999_03
Patent number
US05877174

Reaction notes

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