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

HRID 355450Notes

Reaction equation

HRID 355450 reaction equation
C[O:2][C:3](=O)[C@@H:4]([CH2:15][CH:16]([CH3:18])[CH3:17])[NH:5][P@@:6]([CH3:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7].[NH2:20][O:21][K].Cl>>[OH:21][NH:20][C:3](=[O:2])[C@H:4]([NH:5][P@@:6]([CH3:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])[CH2:15][CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10636698n-((r)-Methylphenylphosphinyl)-d-leucine methyl esterHCID 178514655HCID 178514655, compound

Product 1

HCID 10731747N-hydroxy-2(R)-[[(R)-methylphenylphosphinyl]amino]-4-methylpentanamide

Procedure

N-((R)-Methylphenylphosphinyl)-D-leucine methyl ester (60 mg, 0.21 mmol) is treated with a solution of NH2OK (0.57 mL, 1.76M in methanol) prepared as described in Fieser and Fieser, Vol. 1, p. 478. The reaction is stirred for 7 hours at which time TLC indicates completion. The reaction mixture is neutralized with 1M aqueous HCl and the volatiles are removed. The residue is purified by silica gel flash chromatography (95:5 ethyl acetate:ethanol) to give N-hydroxy-2(R)-[[(R)-methylphenylphosphinyl]amino]-4-methylpentanamide as a colorless solid: MS-IS m/z 285 [M+H]+.

Workup

  1. customprepared
  2. customthe volatiles are removed
  3. customThe residue is purified by silica gel flash chromatography (95:5 ethyl acetate:ethanol)

Sources & evidence

ORD record
ord-39cfabcde4b9475b9ffa9ff106859f14
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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