HCID 178418361, compound → HCID 178479443, compound

HRID 1721005Notes

Reaction equation

HRID 1721005 reaction equation
[ClH:1].C(OC([N:12]1[C:16](=[O:17])[CH2:15][CH2:14][C@H:13]1[C:18]([N:20]1[CH2:37][CH2:36][CH2:35][C@H:21]1[C:22]([NH:24][C@H:25]([CH:33]=[O:34])[CH2:26][CH2:27][CH2:28][NH:29][C:30](=[NH:32])[NH2:31])=[O:23])=[O:19])=O)C1C=CC=CC=1.[H][H]>CN(C)C=O.[Pd]>[ClH:1].[NH:12]1[C:16](=[O:17])[CH2:15][CH2:14][C@H:13]1[C:18]([N:20]1[CH2:37][CH2:36][CH2:35][C@H:21]1[C:22]([NH:24][C@H:25]([CH:33]=[O:34])[CH2:26][CH2:27][CH2:28][NH:29][C:30](=[NH:31])[NH2:32])=[O:23])=[O:19]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178479444HCID 178479444, compound

Product 1

HCID 178479443HCID 178479443, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

After N-benzyloxycarbonyl-L-pyroglutamyl-L-prolyl-L-argininal hydrochloride (0.081 g, 0.15 mmol) was dissolved in dimethlformamide (10 ml), palladium black (1 g) was added to the solution followed by catalytic hydrogenation at room temperature for 30 minutes in a hydrogen flow. After completion of the reaction, the catalyst was filtered off and ether was added to the residue. The precipitated crystals were filtered to give 0.028 g (46%) of L-pyroglutamyl-L-prolyl-L-argininal hydrochloride.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. additionether was added to the residue
  4. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-6d3cae66843e44eea44c3932dba08093
Source dataset
uspto-grants-1996_04
Patent number
US05508385

Reaction notes

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