Diisopropylethylamine → 5-[5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]-1,3-oxazolidin-2-one

HRID 1028519ノート

反応式

HRID 1028519 の反応式
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[C:15]1[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=1[O:24][CH3:25])[OH:4].C(N(C(C)C)CC)(C)C.Cl[C:36](Cl)([O:38]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH:21]([C:19]1[CH:18]=[CH:17][C:16]([O:24][CH3:25])=[C:15]([C:6]2[CH:7]=[CH:8][C:9]([C:11]([F:13])([F:14])[F:12])=[CH:10][C:5]=2[CH:3]2[O:4][C:36](=[O:38])[NH:1][CH2:2]2)[CH:20]=1)([CH3:23])[CH3:22]

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 667170952-Amino-1-[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]ethanol

生成物 1

HCID 591351825-[5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]-1,3-oxazolidin-2-one

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of 0.44 g of 2-amino-1-[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]ethanol in 15 mL of CH2Cl2 was added 0.241 g of diisopropylethylamine, then 0.185 g of triphosgene. The mixture was stirred at 0° C. for 30 min, and then diluted with 30 mL of EtOAc and 20 mL of saturated NaHCO3. The phases were separated and the organic phase was washed with 20 mL of brine, dried (Na2SO4), and concentrated. The residue was purified by flash chromatography on a Biotage Horizon, 40S column, eluting with 1 CV of 5% EtOAc in hexanes, followed by a linear gradient of EtOAc in hexanes from 5 to 100% over 10 CV to provide the title compound. Mass spectrum (ESI) 380.2 (M+1). 1H NMR signals are doubled because of atropoisomerism 1H NMR (500 MHz, CDCl3): δ 7.90, 7.86 (s, 1H), 7.66 (d, J=8 Hz, 1H), 7.35 (d, J=8 Hz, 1H), 7.27 (dd, J=2.5 Hz, 8.5 Hz 1H), 7.03 (d, J=2.5 Hz, 0.5H), 6.87-6.93 (m, 1.5H), 5.65, 5.50 (t, J=8 Hz, 1H), 5.23, 5.09 (s, 1H), 3.75 (s, 1.5H), 3.69 (s, 1.5H), 3.68, 3.51 (t, J=9 Hz, 1H), 3.31, 3.19 (t, J=8.5 Hz, 0.5H), 2.90 (septet, J=7 Hz, 1H), 1.25, 1.24 (d, J=7 Hz, 6H).

後処理

  1. customThe phases were separated
  2. washthe organic phase was washed with 20 mL of brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on a Biotage Horizon, 40S column
  6. washeluting with 1 CV of 5% EtOAc in hexanes

出典と根拠

ORDレコード
ord-2fb617ae641643cab2fcdbab72ea28a3
出典データセット
uspto-grants-2014_05
特許番号
US08735435B2

反応ノート

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