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

HRID 355451노트

반응식

HRID 355451 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6f561e9c76a043c28e7304195cbd909a
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830915

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