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

HRID 355451ノート

反応式

HRID 355451 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6f561e9c76a043c28e7304195cbd909a
出典データセット
uspto-grants-1998_11
特許番号
US05830915

反応ノート

読み込み中…