Hydrochloric Acid → (3R)-1-benzyl-3-(4-methoxybenzyl)piperazine-2,5-dione

HRID 1375041Notes

Reaction equation

HRID 1375041 reaction equation
Cl.[CH2:2]([N:9]([CH2:30]C(OCC1C=CC=CC=1)=O)[C:10](=[O:29])[C@H:11]([NH:21][C:22]([O:24]C(C)(C)C)=O)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:3]1C=C[CH:6]=[CH:5][CH:4]=1.O1CCO[CH2:43][CH2:42]1>ClCCl>[CH2:2]([N:9]1[CH2:30][C:22](=[O:24])[NH:21][C@H:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C:10]1=[O:29])[C:3]1[CH:43]=[CH:42][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 54515673N-benzyl-N-benzyloxycarbonylmethyl-(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propionamide

Product 1

HCID 54330683(3R)-1-benzyl-3-(4-methoxybenzyl)piperazine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4N Hydrogen chloride in 1,4-dioxane solution (48 ml) was added dropwise to a solution of N-benzyl-N-benzyloxycarbonylmethyl-(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propionamide (8.48 g) in dichloromethane (48 ml) under ice-bath cooling. After being stirred for 2 hours at the same temperature, the reaction mixture was concentrated under reduced pressure. The residue was added to aqueous sodium bicarbonate solution (50 ml) and dichloromethane (50 ml), and the organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated under reduced pressure to give a powder of (3R)-1-benzyl-3-(4-methoxybenzyl)piperazine-2,5-dione (3.65 g).

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was added to aqueous sodium bicarbonate solution (50 ml) and dichloromethane (50 ml)
  4. customthe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-113bf4e9bd914ffa97e3ea2e8c1988f9
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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