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

HRID 1382236Notes

Reaction equation

HRID 1382236 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-064c888bd49341769cc04b31932b093c
Source dataset
uspto-grants-1989_02
Patent number
US04806538

Reaction notes

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