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Hydrochloric Acid → HCID 140397789, compound

HRID 1859182
Notes
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Reaction equation

HRID 1859182 reaction equation
[O:1]=[C:2]1[C:7](=[O:8])[NH:6][CH2:5][CH2:4][N:3]1[CH2:9][C:10]([O:12][CH3:13])=[O:11].[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[NH:39])[NH:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[CH:23][CH:22]=1.Cl>O.C(OCC)(=O)C.CN(C)C=O>[CH2:32]([O:31][C:29]([NH:28][C:27]([C:24]1[CH:23]=[CH:22][C:21]([O:20][CH2:19][CH2:18][CH2:17][N:6]2[CH2:5][CH2:4][N:3]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:2](=[O:1])[C:7]2=[O:8])=[CH:26][CH:25]=1)=[NH:39])=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 45115681Methyl (2,3-dioxopiperazin-1-YL)acetateHCID 140397781HCID 140397781, compound

Product 1

HCID 140397789HCID 140397789, compoundYield 36.6%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.2 g of methyl (2,3-dioxopiperazin-1-yl)acetate, 0.26 g of sodium hydride (60%, oil) and 12 ml of N,N-dimethylformamide was stirred at room temperature for 30 minutes. Then, 2.52 g of 1-bromo-3-(4-benzyloxycarbonylamidinophenoxy)propane was added thereto and the resulting mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled and then added to a mixed solvent of 40 ml of ethyl acetate and 40 ml of water. After the pH was adjusted to 1 with 2N hydrochloric acid, the aqueous layer was separated. To the aqueous layer was added 40 ml of ethyl acetate and the pH was adjusted to 10 with potassium carbonate. The organic layer was separated and the aqueous layer was extracted with three 20-ml portions of ethyl acetate. The combined organic layer was washed with water and then a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=30:1) to obtain 1.17 g of methyl [4-[3-(4-benzyloxycarbonylamidinophenoxy)propyl]2,3-dioxopiperazin-1-yl]acetate as a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred at 60° C. for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe aqueous layer was separated
  4. additionTo the aqueous layer was added 40 ml of ethyl acetate
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with three 20-ml portions of ethyl acetate
  7. washThe combined organic layer was washed with water
  8. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-9cdcb29d29834151860e576e8c914179
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06153613

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes