Hydrochloric Acid → HCID 86753756, compound

HRID 1859183Notes

Reaction equation

HRID 1859183 reaction equation
C(OC([NH:11][C:12]([C:14]1[CH:36]=[CH:35][C:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:24](=[O:33])[C:23]2=[O:34])=[CH:16][CH:15]=1)=[NH:13])=O)C1C=CC=CC=1.[ClH:37]>[C].[Pd].CO>[ClH:37].[C:12]([C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:24](=[O:33])[C:23]2=[O:34])=[CH:35][CH:36]=1)(=[NH:11])[NH2:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 140397789HCID 140397789, compound

Product 1

HCID 86753756HCID 86753756, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.05 g of methyl [4-[3-(4-benzyloxycarbonylamidinophenoxy)propyl]-2,3-dioxopiperazin-1-yl]acetate, 0.35 g of 5% palladium-carbon, 0.39 ml of 6N hydrochloric acid and 15 ml of methanol was subjected to hydrogenation at ordinary temperature and atmospheric pressure for 3 hours. Then, the pallasium-carbon was filtered off and the solvent was distilled off under reduced pressure to obtain 0.8 g of methyl [4-[3-(4-amidinophenoxy)propyl]-2,3-dioxopiperazin-1-yl]acetate hydrochloride. The compound obtained was dissolved in 14 ml of 6N hydrochloric acid and the resulting solution was refluxed for 1 hour, after which the solvent was distilled off under reduced pressure to obtain 0.6 g of [4-[3-(4-amidinophenoxy)-propyl]-2,3-dioxopiperazin-1-yl]acetic acid hydrochloride as colorless crystals.

Workup

  1. filtrationThen, the pallasium-carbon was filtered off
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b5bbafb3f638409783dd760e683626d6
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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