Hydrochloric Acid → HCID 22122249, compound

HRID 1417223Notes

Reaction equation

HRID 1417223 reaction equation
C(OC([NH:11][C:12]([C:14]1[CH:55]=[CH:54][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH:29]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:30]([O:32]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:31])[C:25](=[O:52])[C:24]2=[O:53])=[CH:16][CH:15]=1)=[NH:13])=O)C1C=CC=CC=1.Cl>[C].[Pd].CN(C)C=O>[C:12]([C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH:29]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:30]([OH:32])=[O:31])[C:25](=[O:52])[C:24]2=[O:53])=[CH:54][CH:55]=1)(=[NH:11])[NH2:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 140397803HCID 140397803, compound

Product 1

HCID 22122249HCID 22122249, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.25 g of diphenylmethyl α-[4-[4-(4-benzyloxycarbonylamidinophenoxy)butyl]-2,3-dioxopiperazin-1-yl]-α-phenylacetate, 0.13 g of 5% palladium-carbon, 0.34 ml of 1N hydrochloric acid and 5 ml of N,N-dimethylformamide was subjected to hydrogenation at ordinary temperature and atmospheric pressure for 3 hours. Then, the pallasium-carbon was filtered off and the filtrate was concentrated under reduced pressure. To the resulting residue were added 2 ml of ethyl acetate, 5 ml of water and 30 mg of sodium hydrogencarbonate to dissolve the residue. The aqueous layer was separated and then purified by a reversed phase column chromatography (eluent: a 50% aqueous acetonitrile solution) to obtain 0.10 g of α-[4-[4-(4-amidinophenoxy)butyl]-2,3-dioxopiperazin-1-yl]-α-phenylacetic acid as colorless crystals.

Workup

  1. filtrationThen, the pallasium-carbon was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the resulting residue were added 2 ml of ethyl acetate, 5 ml of water and 30 mg of sodium hydrogencarbonate
  4. dissolutionto dissolve the residue
  5. customThe aqueous layer was separated
  6. custompurified by a reversed phase column chromatography (eluent

Sources & evidence

ORD record
ord-d447140c7bf445b6954c70089d9c5e91
Source dataset
uspto-grants-1999_03
Patent number
US05877174

Reaction notes

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