Methanol → HCID 9543420, compound

HRID 355438Notes

Reaction equation

HRID 355438 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.CO.[H][H].CCCCCC>C(OCC)(=O)C.[Pd]>[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

7

Reactant 4

HCID 887MethanolHCID 8058HexaneHCID 10504333HCID 10504333, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9543420HCID 9543420, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyloxy-2(R)-[[(S)-methylphenylphosphinyl]benzylamino]-4-methylpentanamide (334 mg, 0.719 mmol) and 80 mg 10% Pd/C were evacuated in a flask. To this is added 10 mL methanol 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 product is dissolved in ethyl acetate and hexane is added dropwise until the product begins to precipitate to give N-hydroxy-2(R)-[[(R)-methylphenylphosphinyl]benzylamino]-4-methylpentanamide as colorless solid: MS-IS: m/z 375 [M+H]+, 397 [M+Na]+, 413 [M+K]+.

Workup

  1. filtrationThe mixture is filtered through celite
  2. customthe filtrate is collected
  3. customevaporated
  4. customto give a white glassy solid
  5. customto precipitate

Sources & evidence

ORD record
ord-d859ba7b8d7843898c56e5fb153f5206
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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