Diethyl Ether → HCID 18643604, compound

HRID 981394Notes

Reaction equation

HRID 981394 reaction equation
[ClH:1].C([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:32])[C@H:16]([CH2:28][C:29](=[O:31])[NH2:30])[NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=2[OH:26])[CH2:11][CH2:10]1)C1C=CC=CC=1.CCOCC>[H][H].[C].[Pd]>[ClH:1].[OH:26][C:20]1[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:19]=1[C:18]([NH:17][C@H:16]([C:15]([N:12]1[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]1)=[O:32])[CH2:28][C:29](=[O:31])[NH2:30])=[O:27]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 18643643HCID 18643643, compound

Product 1

HCID 18643604HCID 18643604, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

Ethanolic solution (20 ml) of 1-benzyl-4-(2,4-dihydroxybenzoyl-L-asparaginyl)piperazine.hydrochloride (340 mg) was subjected to catalytic reduction in the presence of 10% palladium-carbon (300 mg) for 18 hours at room temperature and under atmospheric pressure in hydrogen stream. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a colorless oily product. This product was powdered with addition of ether and then collected by filtration to obtain 1-(2,4-dihydroxybenzoyl-L-asparaginyl)piperazine.hydrochloride (212 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto obtain a colorless oily product
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3926216593f3408c89898016a6c9a6e2
Source dataset
uspto-grants-1991_02
Patent number
US04990614

Reaction notes

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