N-bromobutanimide → HCID 178472368, 화합물

HRID 928102노트

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HRID 928102 반응식
[OH:1][CH:2]([C:14]1[S:15][CH:16]=[CH:17][N:18]=1)[CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1.C1C(=O)N([Br:26])C(=O)C1>CN(C=O)C>[Br:26][C:16]1[S:15][C:14]([CH:2]([OH:1])[C@H:3]2[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]2)=[N:18][CH:17]=1.[Br:26][C:16]1[S:15][C:14]([CH:2]([OH:1])[C@@H:3]2[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]2)=[N:18][CH:17]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 70983583Ethyl 4-[hydroxy(1,3-thiazol-2-yl)methyl]cyclohexanecarboxylate

생성물 2

HCID 178472368HCID 178472368, 화합물HCID 178472370HCID 178472370, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

The crude mixture of ethyl 4-[hydroxy(1,3-thiazol-2-yl)methyl]cyclohexanecarboxylate (34 g) was diluted with DMF (220 mL) and NBS (23 g, 129 mmol) was added. The resulting mixture was heated to 55° C. and stirred until the starting materials were consumed, at which point the heating mantle was removed. Water (220 mL) containing sodium sulfite (10 g) was added followed by EtOAc. The layers were separated, the organics washed a second time with water, then dried with MgSO4, filtered and concentrated in vacuo. The crude residue was absorbed on silica and purified by flash chromatography to afford racemic ethyl trans-4-[(5-bromo-1,3-thiazol-2-yl)(hydroxy)methyl]cyclohexanecarboxylate as a white solid and racemic ethyl cis-4-[(5-bromo-1,3-thiazol-2-yl)(hydroxy)methyl]cyclohexanecarboxylate as a yellow oil. Characterization data for the trans isomer: MS ESI calc'd. for C13H19BrNO3S [M+H]+ 348, 350. found 348, 350. 1H NMR (600 MHz, CDCl3) δ 7.53 (d, J=4.3, 1H), 4.66 (d, J=5.0, 1H), 4.06 (q, J=7.1, 2H), 2.20-2.16 (m, 1H), 1.97 (d, J=13.3, 2H), 1.80-1.72 (m, 2H), 1.68 (d, J=12.6, 1H), 1.43-1.31 (m, 2H), 1.25-1.13 (m, 5H).

후처리

  1. additionwas added
  2. customwere consumed, at which point the heating mantle
  3. customwas removed
  4. additionWater (220 mL) containing sodium sulfite (10 g)
  5. additionwas added
  6. customThe layers were separated
  7. washthe organics washed a second time with water
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude residue was absorbed on silica
  12. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-c2f1d890926648e0aefecf3f4c9b8184
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290490B2

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