Hydrazine hydrate (1:1) → (S)-3-[[(6-aminohexyl)ethoxyphosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester

HRID 1285473Notes

Reaction equation

HRID 1285473 reaction equation
[CH2:1]([O:3][P:4]([NH:23][C@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:25]1=[O:36])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1C(=O)C2=CC=CC=C2C1=O)=[O:5])[CH3:2].O.NN>O1CCOCC1.C1(C)C=CC=CC=1>[NH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][P:4]([NH:23][C@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:25]1=[O:36])([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86740217(S)-3-[[ethoxy(6-phthalimidohexyl)phosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester

Product 1

HCID 86740218(S)-3-[[(6-aminohexyl)ethoxyphosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-3-[[ethoxy(6-phthalimidohexyl)phosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester in dioxane is treated with hydrazine hydrate and stirred at room temperature under argon. After the reaction is completed, the mixture is diluted with toluene and the solvents decanted. The residue is triturated with methylene chloride and filtered. The combined filtrate is evaporated to dryness to give (S)-3-[[(6-aminohexyl)ethoxyphosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester.

Workup

  1. customthe solvents decanted
  2. customThe residue is triturated with methylene chloride
  3. filtrationfiltered
  4. customThe combined filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-6e11aecd3f0a490cb7bc9efb294199dd
Source dataset
uspto-grants-1986_01
Patent number
US04567167

Reaction notes

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