Trifluoroacetic acid → 7-Hydroxy-8-iodo-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester

HRID 925232ノート

反応式

HRID 925232 の反応式
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O.C1C(=O)N([I:32])C(=O)C1>C(#N)C.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([OH:17])[C:15]([I:32])=[CH:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 584953637-Hydroxy-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester

生成物 1

HCID 867253397-Hydroxy-8-iodo-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester収率 84%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

Into a 100 ml flask, the product of step (c) (503 mg, 2.14 mmol) dissolved in acetonitrile (20 ml) and TFA (2 ml) was added. To this stirred solution, NIS (458 mg, 2.03 mmol) was added. After stirring for 30 minutes at room temperature, the reaction was diluted with water (200 ml) and extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 40% EtOAc in hexanes) gave the sub-title compound as a yellow solid (616 mg). 1H NMR (300 MHz, CDCl3) δ 7.39 (s, 1H); 6.77 (s, 1H); 5.42 (bs, 1H); 4.18 (q, J=7.2 Hz, 2H); 3.61-3.52 (m, 4H); 2.81-2.72 (m, 4H); 1.26 (t, J=6.9 Hz, 3H); MS: ESI (positive): 362 (M+H).

後処理

  1. extractionextracted with EtOAc (3×)
  2. washThe combined EtOAc extracts were washed with brine
  3. dry with materialdried over Na2SO4, and solvent
  4. customevaporated in vacuo
  5. customto give the crude product
  6. customPurification
  7. washby silica-gel chromatography (gradient elution: 0 to 40% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-d044c66b751244ab9a4a336612142775
出典データセット
uspto-grants-2016_03
特許番号
US09284277B2

反応ノート

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