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

HRID 925232노트

반응식

HRID 925232 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d044c66b751244ab9a4a336612142775
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284277B2

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