Nitric Acid → HCID 89778845, 화합물

HRID 1524651노트

반응식

HRID 1524651 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]12[CH2:16][O:15][C@H:14]([CH3:17])[C@H:13]1[C@@H:12]([C:18]([F:21])([F:20])[F:19])[O:11][C:10]([NH2:22])=[N:9]2.[N+:23]([O-])([OH:25])=[O:24]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:23]([O-:25])=[O:24])=[CH:4][C:3]=1[C@:8]12[CH2:16][O:15][C@H:14]([CH3:17])[C@H:13]1[C@@H:12]([C:18]([F:19])([F:20])[F:21])[O:11][C:10]([NH2:22])=[N:9]2

참가 물질

3

반응물 2

HCID 944Nitric AcidHCID 89779019HCID 89779019, 화합물

생성물 1

HCID 89778845HCID 89778845, 화합물수율 84.5%

실험 절차

(4S,4aS,5R,7aS)-7a-(2-fluorophenyl)-5-methyl-4-(trifluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]oxazin-2-amine (Preparation Example 30-(7)) (226 mg, 0.71 mmol) was dissolved in nitric acid (4.80 g, 76.20 mmol). The reaction was then stirred at RT for 90 min. LCMS (Agilent Method A) retention time 3.25 min, ES+: 364 [MH]+. The reaction was concentrated and purified by flash chromatography (Hexane/EtOAc 20-100%). 218 mg (84% yield) of the title compound (85%) and its isomer (15%) were isolated as a mixture.

후처리

  1. concentrationThe reaction was concentrated
  2. custompurified by flash chromatography (Hexane/EtOAc 20-100%)

출처 및 근거

ORD 기록
ord-0734c4cb605345498d7d32693319a1e8
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079914B2

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