(1S,4S)-4-((tert-butoxycarbonyl)amino)-1-isopropylcyclopent-2-enecarboxylic acid → (1S,3R)-3-((Tert-butoxycarbonyl)amino)-1-isopropylcyclopentanecarboxylic acid

HRID 1261636노트

반응식

HRID 1261636 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@:12]([CH:17]([CH3:19])[CH3:18])([C:14]([OH:16])=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:10][CH2:11][C@:12]([CH:17]([CH3:19])[CH3:18])([C:14]([OH:16])=[O:15])[CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 1

HCID 60122256(1S,4S)-4-((tert-butoxycarbonyl)amino)-1-isopropylcyclopent-2-enecarboxylic acid

생성물 1

HCID 60122293(1S,3R)-3-((Tert-butoxycarbonyl)amino)-1-isopropylcyclopentanecarboxylic acid수율 96%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a solution of (1S,4S)-4-[(tert-butoxycarbonyl)amino]-1-isopropylcyclopent-2-ene-1-carboxylic acid (9.78 g, 36.3 mmol) in ethanol (250 mL) was added 10% palladium on carbon (550 mg). The mixture was shaken under hydrogen at 55 psi overnight and filtered through celite. The filtrate was evaporated in vacuo to afford the title compound (9.45 g, 96%). MS calculated for C14H25NO4: (M+H)+ 272; found 172.1 (M-Boc+H)+.

후처리

  1. filtrationfiltered through celite
  2. customThe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-a0a66a1c3e2f43c980d98a41bcefa083
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470827B2

반응 노트

불러오는 중…