HCID 178418361, compound → HCID 178512837, compound

HRID 1721008Notes

Reaction equation

HRID 1721008 reaction equation
C([O:5][CH:6](OCCCC)[C@H:7]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:40])[NH2:39])[NH:8][C:9](=[O:33])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:32])[C@@H:16]1[CH2:20][CH2:19][C:18](=[O:21])[N:17]1C(OCC1C=CC=CC=1)=O)CCC.[H][H]>CO.[Pd]>[NH:17]1[C:18](=[O:21])[CH2:19][CH2:20][C@H:16]1[C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([NH:8][C@H:7]([CH:6]=[O:5])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:40])=[O:33])=[O:32]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178450973HCID 178450973, compound

Product 1

HCID 178512837HCID 178512837, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

After N-benzyloxycarbonyl-L-pyroglutamyl-L-prolyl-L-argininal 1/2 sulfate (0.055 g, 0.10 mmol) was dissolved in 85% methanol (25 ml), a small amount of palladium black (1 g) was added to the solution followed by catalytic hydrogenation at room temperature for an hour in a hydrogen flow. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated. The residue was dissolved in a small amount of methanol and the solution was poured onto an excess of dry ether. The precipitated crystals were filtered to give 0.032 g (77%) of L-pyroglutamyl-L-prolyl-L-argininal.1/2 sulfate.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in a small amount of methanol
  5. additionthe solution was poured onto an excess of dry ether
  6. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-2c865dc3267041b6baaf2aff5af225dc
Source dataset
uspto-grants-1996_04
Patent number
US05508385

Reaction notes

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