Hydrochloric Acid → HCID 13821422, compound

HRID 2165549Notes

Reaction equation

HRID 2165549 reaction equation
C(OC(=O)[C@@H:5]([CH2:29][CH2:30][S:31][CH3:32])[NH:6][C:7](=[O:28])[C@@H:8]([CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([CH3:27])[CH:19]=1)[NH:9][C:10](OC(C)(C)C)=[O:11])C.Cl>C(O)=O>[CH3:27][N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([CH2:17][C@H:8]2[NH:9][C:10](=[O:11])[C@@H:5]([CH2:29][CH2:30][S:31][CH3:32])[NH:6][C:7]2=[O:28])=[CH:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13890975HCID 13890975, compound

Product 1

HCID 13821422HCID 13821422, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

A mixture of N-tert-butoxycarbonyl-1-methyl-D-tryptophyl-D-methionine ethyl ester (2.4 g), formic acid (25 ml), and saturated solution of hydrogen chloride in formic acid (10 ml) was stirred on an ice bath for 1.5 hours. After removal of the solvent, the crude residue was dissolved in ethanol (20 ml) and saturated ammonia in ethanol (10 ml) was added. The resulting mixture was stirred for 16 hours at room temperature and precipitated mass was collected, washed with ethanol, and dried. Recrystallization from ethanol gave (3R,6R)-3-(1-methylindol-3-ylmethyl)-6-(2-methylthioethyl)piperazine-2,5-dione (1.16 g).

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe crude residue was dissolved in ethanol (20 ml)
  3. additionsaturated ammonia in ethanol (10 ml) was added
  4. stirringThe resulting mixture was stirred for 16 hours at room temperature
  5. customprecipitated mass
  6. customwas collected
  7. washwashed with ethanol
  8. customdried
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-01258cc4c7594c01bf046722b4ed94e0
Source dataset
uspto-grants-1990_07
Patent number
US04940709

Reaction notes

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