HCID 19837899, compound → HCID 19837897, compound

HRID 1085008Notes

Reaction equation

HRID 1085008 reaction equation
[CH2:1]([O:3][P:4]([CH2:18][CH:19]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])([CH2:6][N:7]1C(=O)C2=CC=CC=C2C1=O)=[O:5])[CH3:2]>O.NN.C(O)C>[NH2:7][CH2:6][P:4]([CH2:18][CH:19]([CH2:30][CH:31]([CH3:32])[CH3:33])[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])([O:3][CH2:1][CH3:2])=[O:5]

Participants

4

Reactant 1

HCID 19837899HCID 19837899, compound

Product 1

HCID 19837897HCID 19837897, compoundYield 117.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

3 g (6.4 mmol) of benzyl 2(RS)-[[(RS)-(ethoxy)(phthalimidomethyl)phosphinyl]methyl]-4- methylvalerate were dissolved in 39 ml (12.8 mmol) of a 0.33 M solution of hydrazine hydrate in ethanol. The solution was stirred at room temperature overnight. The solvent was removed by evaporation and traces of hydrazine were removed by treatment with toluene followed by evaporation. The residue was taken up in 50 ml of dichloromethane and stirred at room temperature for 45 minutes in the presence of 5 ml of glacial acetic acid. The solid was removed by filtration and the filtrate was evaporated to give 2.56 g of benzyl 2(RS)-[[(RS) -(aminomethyl)(ethoxy)phosphinyl]methyl]-4-methylvalerate in the form of a gum.

Workup

  1. customThe solvent was removed by evaporation and traces of hydrazine
  2. customwere removed by treatment with toluene
  3. customfollowed by evaporation
  4. stirringstirred at room temperature for 45 minutes in the presence of 5 ml of glacial acetic acid
  5. customThe solid was removed by filtration
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-be8b070195a941ad906650f1f8b90b3b
Source dataset
uspto-grants-1991_04
Patent number
US05006651

Reaction notes

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