Cyanogen Bromide → N2-(tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl ester

HRID 379077

반응식

HRID 379077 반응식
[C:1]([O:5][C:6](=[O:20])[C@H:7]([CH2:16][CH2:17][CH2:18][NH2:19])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[N:21]#[C:22]Br.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.[Pd].CCOCC>[C:1]([O:5][C:6](=[O:20])[C@H:7]([CH2:16][CH2:17][CH2:18][NH:19][C:22]#[N:21])[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 7006667(S)-tert-Butyl 5-amino-2-((tert-butoxycarbonyl)amino)pentanoate

생성물 1

HCID 11141515N2-(tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl ester수율 67%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 3283Diethyl Ether용매3회HCID 8857Ethyl Acetate용매

반응 조건

온도
22 °C

실험 절차

To a solution of 6.1 g (14.44 mmol) N5-((Benzyloxy)carbonyl-N2-(tert-butoxycarbonyl-L-ornithine tert-butyl ester in 100 mL ethyl acetate was added 1.0 g 10% palladium on carbon. The suspension was shaken at 22° C. under 50 psi H2 for 45 minutes in a 500 mL Parr bottle. The catalyst was removed by filtration through celite. The resulting solution was concentrated to yield a crude oil. The oil was disolved into 50 mL of diethyl ether and added dropwise to a 0° C. stirred solution of 1.52 g (14.3 mmol) of cyanogen bromide in 30 mL ether. The solution was stirred for 2 h, poured into aqueous sodium bicarbonate, and extraced with ether. The ether solution was dried (magnesium sulfate), concentrated, and purified by silica gel chromatography (100 g, 230-400 mesh silica gel). Elution with a gradient of ethyl acetate in hexanes (30%-60%) gave 3.0 g (67% yield) N2-(tert-butoxycarbonyl)-N5-cyano-L-ornithine tert-butyl ester as an oil.

후처리

  1. customThe catalyst was removed by filtration through celite
  2. concentrationThe resulting solution was concentrated
  3. customto yield a crude oil
  4. additionadded dropwise to a 0° C.
  5. stirringThe solution was stirred for 2 h
  6. dry with materialThe ether solution was dried (magnesium sulfate)
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (100 g, 230-400 mesh silica gel)
  9. washElution with a gradient of ethyl acetate in hexanes (30%-60%)

출처 및 근거

ORD 기록
ord-97fb3c3bc9b749499343e31137bca1de
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297276B1

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