Hydrochloric Acid → HCID 66811572, compound

HRID 1099211Notes

Reaction equation

HRID 1099211 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([O:14]C)=[O:13])[C:7](=[O:22])[C:6]1=[O:23])[CH2:2][CH2:3][CH3:4].[Li+].[OH-].Cl>CO.C1COCC1>[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([OH:14])=[O:13])[C:7](=[O:22])[C:6]1=[O:23])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86639104HCID 86639104, compound

Product 1

HCID 66811572HCID 66811572, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl (4-butyl-2,3-dioxopiperazin-1-yl)(phenyl)acetate (2.5 g, 9.1 mmol) in 1:1 methanol/THF (40 ml) was added 1N LiOH (18.2 ml, 18.2 mmol). The reaction was warmed to rt and allowed to stir for 18 h. The reaction mixture was cooled to 0° C., adjusted to pH 2 with conc HCl, and concentrated in vacuo. The residue was dissolved in EtOAc, washed with brine, dried over sodium sulfate, filtered, and concentrated to yield (4-butyl-2,3-dioxopiperazin-1-yl)(phenyl)acetic acid (100%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6fa2ba61e00e4062a621c6f48c99fcb8
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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