Methanol → HCID 45117257, compound

HRID 1366425Notes

Reaction equation

HRID 1366425 reaction equation
C1(COC([NH:11][C@@H:12]([C:14]([N:16]([CH3:22])[CH2:17][C:18](OC)=[O:19])=[O:15])[CH3:13])=O)C=CC=CC=1.CO>C(Cl)Cl.[Pd]>[CH3:22][N:16]1[CH2:17][C:18](=[O:19])[NH:11][C@H:12]([CH3:13])[C:14]1=[O:15]

Participants

5

Reactant 2

HCID 887MethanolHCID 66936469HCID 66936469, compound

Product 1

HCID 45117257HCID 45117257, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a slurry of three combined batches of methyl N-{[(phenylmethyl)oxy]carbonyl}-D-alanyl-N-methylglycinate (combined total 489.09 g, 1586 mmol) in DCM (210 mL) was added MeOH (1000 mL) and 10% Pd/C (50 g). The mixture was hydrogenated at 50 psi overnight, and then an additional portion of 10% Pd/C (5 g) was added. The mixture was hydrogenated at 50 psi for an additional 6 h, and was then filtered and washed with MeOH and DCM. The resulting clear liquid was evaporated to give a clear oil, which subsequently solidified upon standing to afford (3R)-1,3-dimethyl-2,5-piperazinedione (214.0 g, 95% yield) as a pale yellow tinted solid. LCMS: (M+H)+: 143.0.

Workup

  1. customwas hydrogenated at 50 psi overnight
  2. filtrationwas then filtered
  3. washwashed with MeOH and DCM
  4. customThe resulting clear liquid was evaporated
  5. customto give a clear oil, which

Sources & evidence

ORD record
ord-41136c3eabb441669ba210fe3012b107
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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