Imidazole → HCID 58747916, 화합물

HRID 1942572노트

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HRID 1942572 반응식
[CH2:1]([O:8][C@@H:9]([C@H:12]([C@@H:21]([CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:22])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[CH3:37][C:38]([Si:41](Cl)([CH3:43])[CH3:42])([CH3:40])[CH3:39]>CN(C=O)C>[CH2:1]([O:8][C@@H:9]([C@H:12]([C@@H:21]([CH2:23][O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[OH:22])[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:10][O:11][Si:41]([C:38]([CH3:40])([CH3:39])[CH3:37])([CH3:43])[CH3:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58747826HCID 58747826, 화합물

생성물 1

HCID 58747916HCID 58747916, 화합물수율 93%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

A mixture of 239 (5.24 g, 12.4 mmol), imidazole (3.72 g, 54.6 mmol), and TBDMSCl (2.07 g, 13.6 mmol) in dry DMF (50 mL) was stirred at 0° C. under N2 for 30 min. The reaction was quenched with ice (20 mL), and the reaction mixture was partitioned between Et2O (200 mL) and H2O (100 mL). The separated organic phase was washed with H2O (100 mL) and brine (100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash chromatography (hexanes:EtOAc, 3:1) to give a colorless oil 240 (6.164 g, 93%): [α]D −140.4° (c 0.87, CHCl3); 1H NMR (CDCl3) δ 7.35-7.25 (15H, m, Ar), 4.74 and 4.60 (2H, 2d, Ja,b=11.7 Hz, CH2Ph), 4.69 and 4.51 (2H, 2d, Ja,b=11.9 Hz, CH2Ph), 4.51 and 4.45 (2H, 2d, Ja,b=11.6 Hz, CH2Ph), 4.05 (1H, dddd, J3,4=2.3 Hz, J4,5a=J4,5b=5.9 H,J4,OH=5.9 Hz, H-4), 3.88 (1H, dd, J1a,1b=11.0 Hz, J1a,2=4.2 Hz, H-1a), 3.78 (1H, dd, J1b,2=4.9 Hz, H-1b), 3.77 (1H, dd, J2,3=4.1 Hz, H-3), 3.73 (1H, ddd, H-2), 3.54(1H, dd, H-5a), 3.49 (1H, dd, H-5b), 3.02 (1H, d, OH), 0.891 (9H, s, (CH3)3CSi), 0.05 (6H, s, (CH3)2Si); 13C NMR (CDCl3) δ 149.11, 145.62, 140.95 (3Cipso), 128.35-127.60 (15C, Ar), 80.25 (C-2), 77.25 (C-3), 73.65, 73.26, 72.84 (3CH2Ph), 71.16 (C-5), 69.75 (C-4), 62.04 (C-1), 25.88 (3C, (CH3)3CSi) 18.23 (1C, CSi), −5.40, −5.44 (2C, (CH3)2Si); MALDI-TOF MS: m/e 537.89 (M++H), 559.33 (M++Na). Anal. Calcd for C32H44O5Si: C, 71.60; H, 8.26. Found: C, 71.44; H, 8.34.

후처리

  1. customThe reaction was quenched with ice (20 mL)
  2. customthe reaction mixture was partitioned between Et2O (200 mL) and H2O (100 mL)
  3. washThe separated organic phase was washed with H2O (100 mL) and brine (100 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (hexanes:EtOAc, 3:1)

출처 및 근거

ORD 기록
ord-9b24d2181d3b43a6ad5ca06ec10f7363
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389565B2

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