Trifluoroacetic acid → (4S,6S)-4-(5-bromo-2-methoxypyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

HRID 930383ノート

反応式

HRID 930383 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C@:10]2([CH3:28])[CH2:15][C@@H:14]([C:16]([F:19])([F:18])[F:17])[O:13][C:12]([NH:20]C(=O)OC(C)(C)C)=[N:11]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.FC(F)(F)C(O)=O>>[Br:1][C:2]1[CH:3]=[C:4]([C@:10]2([CH3:28])[CH2:15][C@@H:14]([C:16]([F:18])([F:19])[F:17])[O:13][C:12]([NH2:20])=[N:11]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

参加物

3

反応物 2

HCID 6422Trifluoroacetic acidHCID 86732211tert-Butyl ((4S,6S)-4-(5-bromo-2-methoxypyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)carbamate

生成物 1

HCID 86732212(4S,6S)-4-(5-bromo-2-methoxypyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine収率 83.1%

実験手順

tert-Butyl ((4S,6S)-4-(5-bromo-2-methoxypyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)carbamate (0.56 g, 1.196 mmol) was treated with trifluoroacetic acid, 99% (10 ml, 135 mmol) and the mixture was stirred at room temperature for 15 min. The solvent was removed and the residue was worked up with saturated sodium bicarbonate solution and extracted with dichloromethane three times. The combined organic layers were dried on sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography using a gradient of 10-60% EtOAc/hexane to give (4S,6S)-4-(5-bromo-2-methoxypyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (0.366 g, 0.994 mmol, 83% yield).

後処理

  1. customThe solvent was removed
  2. extractionextracted with dichloromethane three times
  3. customThe combined organic layers were dried on sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by column chromatography

出典と根拠

ORDレコード
ord-1ffa701ff67d4e19b9ddc45add725488
出典データセット
uspto-grants-2016_03
特許番号
US09296734B2

反応ノート

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