Sodium Azide → [5-(3-Azido-phenyl)-5-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

HRID 81529

반응식

HRID 81529 반응식
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18](Br)[CH:17]=2)([CH2:14][F:15])[N:13]=1)([CH3:4])([CH3:3])[CH3:2].[N-:24]=[N+:25]=[N-:26].[Na+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].CNC1CCCCC1NC>[Cu]I.O.CCO>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:24]=[N+:25]=[N-:26])[CH:17]=2)([CH2:14][F:15])[N:13]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 33557Sodium AzideHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 23667548Sodium AscorbateHCID 66665441HCID 66665441, 화합물

생성물 1

HCID 86650252[5-(3-Azido-phenyl)-5-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

A suspension of [5-(3-bromo-phenyl)-5-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (114 mg, 0.295 mmol), NaN3 (77 mg, 1.18 mmol), CuI (11 mg, 0.059 mmol), sodium ascorbate (12 mg, 0.059 mmol), N,N′-dimethyl-cyclohexane-1,2-diamine (13 mg, 0.089 mmol), 1.5 ml of EtOH and 0.6 ml of water was stirred under N2 at 90° C. for 1 h. The mixture was filtered through Celite, and the filtrate was chromatographed on silica gel (cyclohexane/EtOAc=6:1) to yield the title compound in the form of a colourless foam. TLC (hexane/EtOAc=3:1): Rf=0.33; HPLC: RtH1=2.258 min; 1H-NMR (400 MHz, CDCl3); 7.40-6.88 (m, 4H; broad signals due to rotamers), 4.75-3.60 (m, 6H), 1.42 (br, 9H); MS: 350 [(M+H)+].

후처리

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was chromatographed on silica gel (cyclohexane/EtOAc=6:1)

출처 및 근거

ORD 기록
ord-67af881384a140ab88b90ebf61602208
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846658B2

연결된 노트

불러오는 중…