2-Bromoethanol → HCID 86684665, 화합물

HRID 1504357노트

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HRID 1504357 반응식
[Br:1][CH2:2][CH2:3][OH:4].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH:24]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:25]([C:34]([O:36][CH3:37])=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][CH2:2][CH2:3][O:4][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][C@H:25]([NH:24][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1

참가 물질

6

반응물 4

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 7019130Boc-Tyr-OMe

생성물 1

HCID 86684665HCID 86684665, 화합물수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

2-Bromo-ethanol (0.61 mL, 8.03 mmol), followed by PPh3 (3.16 g, 12.05 mmol) was added to a solution of Boc-Tyr-OMe (2.85 g, 9.64 mmol) in anhydrous THF (50 mL). The mixture was cooled to 0° C. and DEAD (5.5 mL of 40% wt solution in toluene, 12.05 mmol) was added. The mixture was allowed to warm at room temperature and was stirred overnight. After the reaction was finished, the solvent was evaporated and the residue dissolved in EtOAc (100 mL) was washed with NaOH (0.1 M, 2×50 mL), followed by brine. The organic phase was dried over Na2SO4 and evaporated. The crude product was purified by flash column chromatography (SiO2, step-wise gradient from 2-40% EtOAc in Hexanes) to give 1A (1.61 g, 50%) as a white solid. 1H NMR (600 MHz, CDCl3): δ 7.04 (2H, d, J=8.4 Hz), 6.84 (2H, d, J=8.4 Hz), 4.96 (1H, d, J=7.8 Hz), 4.51-4.58 (1H, m), 4.27 (2H, t, J=6.6 Hz), 3.71 (3H, s), 3.62 (2H, t, J=6.6 Hz), 3.06 (1H, dd, J=13.8, 5.4 Hz), 3.00 (1H, dd, J=13.8, 5.4 Hz), 1.42 (9H, s); 13C NMR (150 MHz, CDCl3): δ 172.3, 157.2, 155.1, 130.4, 128.8, 114.8, 79.9, 67.9, 54.5, 52.2, 37.5, 29.1, 28.3; MS (ESI, m/z): 424 (M+Na)+.

후처리

  1. temperatureto warm at room temperature
  2. customthe solvent was evaporated
  3. dissolutionthe residue dissolved in EtOAc (100 mL)
  4. washwas washed with NaOH (0.1 M, 2×50 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated
  7. customThe crude product was purified by flash column chromatography (SiO2, step-wise gradient from 2-40% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-de0c5e1355c9413b8ea25cf6b6621de1
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212381B2

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