Hydrochloric Acid → (3R,6S)-3-benzyl-6-methylthiomethylpiperazine-2,5-dione

HRID 2165550Notes

Reaction equation

HRID 2165550 reaction equation
C(OC(=O)[C@@H:5]([CH2:25][S:26][CH3:27])[NH:6][C:7](=[O:24])[C@@H:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:9][C:10](OC(C)(C)C)=[O:11])C.Cl>C(OCC)(=O)C>[CH2:17]([C@H:8]1[NH:9][C:10](=[O:11])[C@@H:5]([CH2:25][S:26][CH3:27])[NH:6][C:7]1=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57067798HCID 57067798, compound

Product 1

HCID 13821426(3R,6S)-3-benzyl-6-methylthiomethylpiperazine-2,5-dioneYield 30.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of N-tert-butoxycarbonyl-D-phenylalanyl-S-methyl-D-cysteine ethyl ester (0.41 g), ethyl acetate (10 ml), and saturated solution of hydrogen chloride in ethyl acetate (10 ml) was stirred for 4 hours at room temperature. After removal of the solvent, the residue was dissolved in ethanol (10 ml) and saturated ammonia in ethanol (10 ml) was added to the solution. The resulting mixture was stirred for 17 hours at room temperature and the solvent was evaporated off. Recrystallization from acetic acid gave (3R,6S)-3-benzyl-6-methylthiomethylpiperazine-2,5-dione (0.08 g).

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in ethanol (10 ml)
  3. additionsaturated ammonia in ethanol (10 ml) was added to the solution
  4. stirringThe resulting mixture was stirred for 17 hours at room temperature
  5. customthe solvent was evaporated off
  6. customRecrystallization from acetic acid

Sources & evidence

ORD record
ord-d1f3ced8a7834855b23bb74a8c2e3796
Source dataset
uspto-grants-1990_07
Patent number
US04940709

Reaction notes

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