Hydrochloric Acid → (2R)-2-[benzyl(dimethylphosphoryl)amino]-N-hydroxy-4-methylpentanamide

HRID 355442Notes

Reaction equation

HRID 355442 reaction equation
C[O:2][C:3](=O)[C@@H:4]([CH2:17][CH:18]([CH3:20])[CH3:19])[N:5]([P:13]([CH3:16])([CH3:15])=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:22][O:23][K].Cl>>[OH:23][NH:22][C:3](=[O:2])[C@H:4]([N:5]([P:13]([CH3:16])([CH3:15])=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:17][CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10686470n-(Dimethylphosphinyl)-n-benzyl-d-leucine methyl esterHCID 178514655HCID 178514655, compound

Product 1

HCID 10852576(2R)-2-[benzyl(dimethylphosphoryl)amino]-N-hydroxy-4-methylpentanamide

Procedure

N-(Dimethylphosphinyl)-N-benzyl-D-leucine methyl ester (158 mg, 0.51 mmol) is treated with a solution of NH2OK (2.8 mL, 1.76M in methanol) prepared as described in Fieser and Fieser, Vol. 1, p. 478). The reaction is allowed to stir 3 hours at room temperature at which time is determined complete by TLC. The reaction mixture is neutralized with 1M aqueous HCl; the volatiles are removed until the product oils out. Methanol is then added followed by water dropwise until the solution appears cloudy. The crystals are collected by filtration to give N-hydroxy-2(R)-[[dimethylphosphinyl]benzylamino]-4-methyl-pentanamide as a colorless solid: MS-IS m/z 313 [M+H]+, 335 [M+Na]+, 357 [M+K]+. (R2 =isobutyl, R1 =benzyl, R3 =methyl, R4 =phenyl).

Workup

  1. customprepared
  2. customthe volatiles are removed until the product oils out
  3. additionMethanol is then added
  4. filtrationThe crystals are collected by filtration

Sources & evidence

ORD record
ord-b01e5df2739740dda5eaa8641be37713
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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