Hydrochloric Acid → (2R)-N-hydroxy-4-methyl-2-{[methyl(phenyl)phosphoryl]amino}pentanamide

HRID 355451Notes

Reaction equation

HRID 355451 reaction equation
[CH3:1][P@@:2]([NH:10][CH:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([NH2:14])=[O:13])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].C[O:20]C(=O)[C@@H](CC(C)C)N[P@](C)(C1C=CC=CC=1)=O.NO[K].Cl>>[OH:20][NH:14][C:12](=[O:13])[C@H:11]([NH:10][P@:2]([CH3:1])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3])[CH2:15][CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10755403N-((S)-Methylphenylphosphinyl)-D-leucine methyl esterHCID 86753295[[(S)-methylphenylphosphinyl]amino]-4-methylpentanamideHCID 178514655HCID 178514655, compound

Product 1

HCID 10541018(2R)-N-hydroxy-4-methyl-2-{[methyl(phenyl)phosphoryl]amino}pentanamide

Procedure

N-Hydroxy-2)-[[(S)-methylphenylphosphinyl]amino]-4-methylpentanamide: N-((S)-Methylphenylphosphinyl)-D-leucine methyl ester (55 mg, 0.19 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 6 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 (80:20 ethyl acetate:ethanol) followed by crystallization from ethyl acetate/hexane to give N-hydroxy-2(R)-[[(S)-methylphenylphosphinyl]amino]-4-methylpentanamide as a colorless solid: MS-IS m/z 285 [M+H]+.(R1 =H, R2 =isobutyl, R3 =methyl, R4 =phenyl).

Workup

  1. customprepared
  2. customthe volatiles are removed
  3. customThe residue is purified by silica gel flash chromatography (80:20 ethyl acetate:ethanol)
  4. customfollowed by crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-6f561e9c76a043c28e7304195cbd909a
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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