Hydrochloric Acid → HCID 54437783, compound

HRID 1765989Notes

Reaction equation

HRID 1765989 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([NH:15][C:16](=[O:19])[CH2:17]Cl)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([O:13][CH3:14])[CH:7]=1.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.ClCCl>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([NH:15][C:16](=[O:19])[CH2:17][NH:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([O:13][CH3:14])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 54076724HCID 54076724, compound

Product 1

HCID 54437783HCID 54437783, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of (2R)-2-[N-(chloroacetyl)amino]-3-(3-methoxy-4-methylphenyl)propionic acid methyl ester (1.85 g) in N,N-dimethylformamide (15 ml) were added successively benzylamine (1.65 g) and potassium carbonate (1.28 g) at 20° C. After stirring at 35° C. for 1.5 hour, the mixture was poured into a mixture of ice-water (20 ml) and dichloromethane (20 ml). After adjusting the mixture to pH 9 with a diluted aqueous hydrochloric acid solution with stirring, the organic layer was separated, washed with an aqueous sodium chloride solution (20 ml), dried over magnesium sulfate and the solvent was evaporated under reduced pressure to give (2R)-2-[N-(benzylaminoacetyl)amino]-3-(3-methoxy-4-methylphenyl)-propionic acid methyl ester in the form of an oily substance. A solution of (2R)-2-[N-(benzylaminoacetyl)-amino]-3-(3-methoxy-4-methylphenyl)propionic acid methyl ester obtained by the above process and acetic acid (0.18 ml) in isopropyl alcohol (10 ml) was stirred under reflux for 12 hours. After cooling the mixture to room temperature, isopropyl ether was added to the mixture. The produced precipitates were collected by filtration and washed with isopropyl ether to give (3R)-1-benzyl-3-(3-methoxy-4-methylbenzyl)piperazine-2,5-dione (1.45 g) in the form of colorless crystals.

Workup

  1. stirringwith stirring
  2. customthe organic layer was separated
  3. washwashed with an aqueous sodium chloride solution (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bcbeacf873e44d1ab6ac4cc27f0f210b
Source dataset
uspto-grants-2007_06
Patent number
US07229992B2

Reaction notes

Loading…