Hydrochloric Acid → HCID 53791729, compound

HRID 2288220Notes

Reaction equation

HRID 2288220 reaction equation
[CH2:1]([N:8]([CH2:28][C:29]([O:31]CC1C=CC=CC=1)=O)[C:9](=[O:27])[C@H:10]([NH:19]C(OC(C)(C)C)=O)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>ClCCl.O1CCOCC1>[CH2:1]([N:8]1[CH2:28][C:29](=[O:31])[NH:19][C@H:10]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C:9]1=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54483553HCID 54483553, compound

Product 1

HCID 53791729HCID 53791729, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To an ice-cooled solution of (2R)-N-benzyl-N-benzyloxycarbonylmethyl-2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)propanamide (9.48 g) in dichloromethane (55 ml) was added 4N hydrogen chloride in dioxane solution (54.6 ml). The mixture was stirred at the same temperature for 15 minutes and at room temperature for one hour. After removal of solvent by evaporation, excess aqueous sodium hydrogen carbonate solution was added to the resulting residue. The mixture was warmed at near 50° C. for several minutes and the resulting precipitates were collected by filtration and washed with water and dried in vacuo to give (3R)-1-benzyl-3-(4-fluorobenzyl)piperazine-2,5-dione (5.00 g).

Workup

  1. customAfter removal of solvent
  2. customby evaporation, excess aqueous sodium hydrogen carbonate solution
  3. additionwas added to the resulting residue
  4. temperatureThe mixture was warmed at near 50° C. for several minutes
  5. customthe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-717dd6ad5477422a978a4f92c2add7a4
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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