Hydrochloric Acid → HCID 22122267, compound

HRID 1859176Notes

Reaction equation

HRID 1859176 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH:12]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH2:13][C:14]([O:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[C:8](=[O:36])[C:7]1=[O:37])=[N+]=[N-].Cl.CN(C)C=O.C(=O)([O-])O.[Na+]>[C].[Pd].C(Cl)Cl>[NH2:1][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH:12]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH2:13][C:14]([O:16][CH:17]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[C:8](=[O:36])[C:7]1=[O:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 22122152HCID 22122152, compound

Product 1

HCID 22122267HCID 22122267, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.7 g of diphenylmethyl 3-[4-(2-azidoethyl)-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)-propionate, 0.13 g of 5% palladium-carbon, 2.8 ml of 1N hydrochloric acid and 7 ml of N,N-dimethylformamide was subjected to hydrogenation at ordinary temperature and atmospheric pressure for 2 hours. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. To the resulting residue were added 5 ml of diethyl ether and 1 ml of ethyl acetate and the resulting mixture was filtered to obtain a white solid. The solid obtained was added to a mixed solvent of 20 ml of methylene chloride and 10 ml of a saturated aqueous sodium hydrogencarbonate solution and stirred for 10 minutes. The organic layer was separated and the aqueous layer was extracted with two 10-ml portions of methylene chloride. The combined organic layer was washed with water and then a saturated aqueous sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 0.2 g of diphenylmethyl 3-[4-(2-aminoethyl)-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)-propionate as a brown oil.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the resulting residue were added 5 ml of diethyl ether and 1 ml of ethyl acetate
  5. filtrationthe resulting mixture was filtered
  6. customto obtain a white solid
  7. customThe solid obtained
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with two 10-ml portions of methylene chloride
  10. washThe combined organic layer was washed with water
  11. dry with materialAfter drying over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d1f640eec7794022b2d84a390cc65eca
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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