Azane;hydrate → HCID 70453091, compound

HRID 280793Notes

Reaction equation

HRID 280793 reaction equation
[CH2:1]([P:8]([NH:17][C@H:18]([C:20]([N:22]1[CH2:36][CH2:35][CH2:34][C@H:23]1[C:24]([N:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28]([OH:30])=[O:29])=[O:25])=[O:21])[CH3:19])(CC1C=CC=CC=1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].O.N>C(O)C.O.C(O)(=O)C.[C].[Pd]>[CH2:1]([P:8](=[N:17][C@H:18]([C:20]([N:22]1[CH2:36][CH2:35][CH2:34][C@H:23]1[C:24]([N:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28]([OH:30])=[O:29])=[O:25])=[O:21])[CH3:19])=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 12896473Azane;hydrateHCID 13503349HCID 13503349, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70453091HCID 70453091, compoundYield 34.2%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Dibenzylphosphoryl-L-alanyl-L-prolyl-L-proline (1.63 g, 3 mmole) was dissolved in a mixture of ethyl alcohol (50 ml), water (10 ml) and acetic acid (0.1 ml), and 5% palladium-carbon (200 mg) was added thereto. Hydrogen gas was passed through the mixture for 5 minutes while vigorously stirring. To the solution, concentrated ammonia water (1 ml) was added, and then the catalyst was removed by filtration. The filtrate was concentrated to an oily residue. This was dissolved in 1N ammonia water, and the thus obtained solution was passed through a column packed with a resin of porous polystyrene-divinylbenzene, HP-20, produced by Mitsubishi Chemical Industries LTD. The product was eluted from the column with acetonitrile solution, whose concentration was changed linearly from 1N NH3 water to 1N NH3 water, containing 33% acetonitrile. The main fractions were collected and the solvent was distilled off to obtain monobenzylphosphoryl-L-alanyl-L-prolyl-L-proline (430 mg, yield: 29.4%).

Workup

  1. additionwas added
  2. customthe catalyst was removed by filtration
  3. concentrationThe filtrate was concentrated to an oily residue
  4. dissolutionThis was dissolved in 1N ammonia water
  5. customproduced by Mitsubishi Chemical Industries LTD
  6. washThe product was eluted from the column with acetonitrile solution, whose concentration
  7. additioncontaining 33% acetonitrile
  8. customThe main fractions were collected
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-a45785ed10d6468d8dc37fe68bd86d04
Source dataset
uspto-grants-1986_05
Patent number
US04590178

Reaction notes

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