Hydrazine hydrate (1:1) → (aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid methyl ester acetate

HRID 1084989Notes

Reaction equation

HRID 1084989 reaction equation
[CH3:1][O:2][P:3]([CH2:17][CH:18]([C:24](=[O:35])[NH:25][C@H:26]([C:31](=[O:34])[NH:32][CH3:33])[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:19][C:20](C)([CH3:22])[CH3:21])([CH2:5][N:6]1C(=O)C2=CC=CC=C2C1=O)=[O:4].[OH2:36].NN>CO>[C:31]([OH:34])(=[O:36])[CH3:26].[CH3:1][O:2][P:3]([CH2:5][NH2:6])([CH2:17][CH:18]([C:24](=[O:35])[NH:25][C@H:26]([C:31](=[O:34])[NH:32][CH3:33])[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54363570[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]-4-methylpentyl](phthalimidomethyl)phosphinic acid methyl ester

Product 1

HCID 86743557(aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid methyl ester acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5 g of [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]-4-methylpentyl](phthalimidomethyl)phosphinic acid methyl ester, prepared as described in Example 1(A)(v), were dissolved in 30 ml of a 0.33 M solution of hydrazine hydrate in methanol. The mixture was stirred at room temperature for 18 hours and was then evaporated. The residue was suspended in 50 ml of dichloromethane and 0.7 g of glacial acetic acid was added. After standing at room temperature for 1 hour the precipitated phthalhydrazide was removed by filtration and the filtrate was evaporated to give a colorless gum which was purified by chromatography on silica gel using chloroform/methanol/acetic acid/water (60:18:2:3) for the elution. There were obtained 1.84 g of (aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid methyl ester acetate in the form of a colorless gum.

Workup

  1. customwas then evaporated
  2. addition0.7 g of glacial acetic acid was added
  3. waitAfter standing at room temperature for 1 hour
  4. customthe precipitated phthalhydrazide was removed by filtration
  5. customthe filtrate was evaporated
  6. customto give a colorless gum which
  7. customwas purified by chromatography on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-104002031e9e4073aeb281a8ece41052
Source dataset
uspto-grants-1991_04
Patent number
US05006651

Reaction notes

Loading…