Nitric Acid → HCID 89778845, compound

HRID 1524651Notes

Reaction equation

HRID 1524651 reaction equation
[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

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 89779019HCID 89779019, compound

Product 1

HCID 89778845HCID 89778845, compoundYield 84.5%

Procedure

(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.

Workup

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

Sources & evidence

ORD record
ord-0734c4cb605345498d7d32693319a1e8
Source dataset
uspto-grants-2015_07
Patent number
US09079914B2

Reaction notes

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