HCID 10504333, compound → HCID 9543420, compound

HRID 355439Notes

Reaction equation

HRID 355439 reaction equation
C([O:8][NH:9][C:10](=[O:33])[C@H:11]([N:16]([P@:24]([CH3:32])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:12][CH:13]([CH3:15])[CH3:14])C1C=CC=CC=1.[H][H]>[Pd].CO>[OH:8][NH:9][C:10](=[O:33])[C@H:11]([N:16]([P@@:24]([CH3:32])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:25])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 10504333HCID 10504333, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9543420HCID 9543420, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-Benzyloxy-2(R)-[[(S)-methylphenylphosphinyl]benzylamino]-4-methylpentanamide (460 mg, 0.99 mmol) and 10% Pd/C (100 mg) are evacuated in a flask. To this is added methanol (10 mL) and a hydrogen atmosphere is introduced. The reaction is allowed to stir at room temperature for 2 hours at which time the reaction appears complete by TLC. The mixture is filtered through celite; the filtrate is collected and evaporated to give a white glassy solid. The hydroxamic acid is crystallized by dissolving in ethyl acetate and adding hexane dropwise until the solution becomes cloudy. N-Hydroxy-2(R)-[[(R)-methylphenyl-phosphinyl]benzylamino]-4-methylpentanamide is obtained as a white crystalline solid: MS-IS m/z 375 [M+H]+, 397 [M+Na]+, 413 [M+K]+. (R2 =isobutyl, R1 =benzyl, R3 =methyl, R4 =phenyl).

Workup

  1. filtrationThe mixture is filtered through celite
  2. customthe filtrate is collected
  3. customevaporated
  4. customto give a white glassy solid
  5. customThe hydroxamic acid is crystallized
  6. dissolutionby dissolving in ethyl acetate
  7. additionadding hexane dropwise until the solution

Sources & evidence

ORD record
ord-9e2864a6e5df49c7881e3bc203a136f6
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

Loading…