Sodium 4-methyl-2-oxovalerate → N-(1-Carboxy-3-methylbutyl)-L-alanyl-L-isoleucine

HRID 1758836

반응식

HRID 1758836 반응식
[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:12]([OH:14])=[O:13])[C@H:8]([CH2:10][CH3:11])[CH3:9])=[O:5])[CH3:3].[Na+].[CH3:16][CH:17]([CH3:24])[CH2:18][C:19](=O)[C:20]([O-:22])=[O:21].C([BH3-])#N.[Na+]>O>[C:20]([CH:19]([NH:1][C@H:2]([C:4]([NH:6][C@H:7]([C:12]([OH:14])=[O:13])[C@H:8]([CH2:10][CH3:11])[CH3:9])=[O:5])[CH3:3])[CH2:18][CH:17]([CH3:24])[CH3:16])([OH:22])=[O:21]

참가 물질

5

반응물 3

HCID 4137900Sodium 4-methyl-2-oxovalerateHCID 5003444Sodium cyanoborohydrideHCID 7408079Ala-Ile

생성물 1

HCID 53653027N-(1-Carboxy-3-methylbutyl)-L-alanyl-L-isoleucine수율 85.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of L-alanyl-L-isoleucine (150 mg) and 4-methyl-2-oxopentanoic acid sodium salt (564 mg) in water was adjusted to pH 7 and treated with 140 mg of sodium cyanoborohydride at room temperature for several days. The reaction was quenched with strong acid ion-exchange resin, added to a column of the same resin, and eluted with 2% pyridine in water. Freeze drying afforded 200 mg (84.9%) of white fluffy solid, N-(1-carboxy-3-methylbutyl)-L-alanyl-L-isoleucine. Mass spectrum showed peaks at 460 for the disilylated derivative, and 445 for disilyl molecular ion minus methyl (460-15). The nmr spectrum showed a broad doublet centered at 0.95 ppm, complex absorption in the 1.2-1.8 ppm range, and a broad weak singlet at 3.7 ppm.

후처리

  1. customThe reaction was quenched with strong acid ion-exchange resin
  2. additionadded to a column of the same resin
  3. washeluted with 2% pyridine in water
  4. customFreeze drying

출처 및 근거

ORD 기록
ord-ea3cb8a871d64c27860694e436ac4ae7
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04374829

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