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Hydrochloric Acid → (S)-4-(4-Amidinobenzoylglycyl)-3-methoxycarbonylmethyl-2-oxopiperazine-1-acetic acid hydrochloride

HRID 487429
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Reaction equation

HRID 487429 reaction equation
C([O:5][C:6](=[O:34])[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:27])[CH2:15][NH:16][C:17]([O:19]CC2C=CC=CC=2)=O)[C@@H:10]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:9]1=[O:33])(C)(C)C.[H][H].[ClH:37].[C:38]([C:41]1[CH:49]=[CH:48][C:44](C(O)=O)=[CH:43][CH:42]=1)(=[NH:40])[NH2:39].Cl.CN(C)CCCN=C=NCC.FC(F)(F)C(O)=O.Cl>CO.CN(C)C=O.C(OCC)(=O)C.C(Cl)Cl.[C].[Pd]>[ClH:37].[C:38]([C:41]1[CH:49]=[CH:48][C:44]([C:17]([NH:16][CH2:15][C:14]([N:11]2[CH2:12][CH2:13][N:8]([CH2:7][C:6]([OH:5])=[O:34])[C:9](=[O:33])[C@@H:10]2[CH2:28][C:29]([O:31][CH3:32])=[O:30])=[O:27])=[O:19])=[CH:43][CH:42]=1)(=[NH:39])[NH2:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

12

Reactant 6

HCID 313Hydrochloric Acid2×HCID 6422Trifluoroacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 448908304-Amidinobenzoic acid hydrochlorideHCID 54519104(S)-4-(N-benzyloxycarbonylglycyl)-3-methoxycarbonylmethyl-2-oxo-piperazine-1-acetic acid t-butyl ester
HCID 178418361
HCID 178418361, compound

Product 1

HCID 9890862(S)-4-(4-Amidinobenzoylglycyl)-3-methoxycarbonylmethyl-2-oxopiperazine-1-acetic acid hydrochlorideYield 53.4%

Reagents, catalysts & solvents 5

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 10 ml of methanol was dissolved 480 mg of (S)-4-(N-benzyloxycarbonylglycyl)-3-methoxycarbonylmethyl-2-oxo-piperazin-1-acetic acid t-butyl ester obtained in Working Example 58. To the solution was added 100 mg of 10% palladium-carbon, and the mixture was stirred for one hour at room temperature in a hydrogen streams. The catalyst was filtered off, and the filtrate was concentrated to give an oily product, which was dissolved in 5 ml of dimethylformamide. To the solution were added 200 mg of 4-amidinobenzoic acid hydrochloride, then 200 mg of (1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride. The mixture was stirred for one hour at room temperature. The reaction mixture was diluted with ethyl acetate, washed with a 5% aqueous solution of potassium hydrogensulfate, then a 10% aqueous solution of sodium hydrogencarbonate, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure to leave an oily product. The oily product was dissolved in 5 ml of methylene chloride. To the solution was added 5 ml of trifluoroacetic acid, and the mixture was stirred for one hour at room temperature. The reaction mixture was concentrate to give a crude product, which was made into hydrochloride with 1N HCl, followed by purification by means of a C18 --ODS column to afford 250 mg of the title compound as colorless powder.

Workup

  1. customobtained in Working Example 58
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. customto give an oily product, which
  5. washwashed with a 5% aqueous solution of potassium hydrogensulfate
  6. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  7. customto leave an oily product
  8. stirringthe mixture was stirred for one hour at room temperature
  9. concentrationThe reaction mixture was concentrate
  10. customto give a crude product, which
  11. customfollowed by purification by means of a C18

Sources & evidence

ORD record
ord-248725e234ea48e3a3a7235f93440a43
Source dataset
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05294713

Reaction notes

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