tert-Butanol → tert-Butyl 1-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate

HRID 1878720노트

반응식

HRID 1878720 반응식
[Si:1]([O:8][CH2:9][C:10]([N:13]1[C:18](=[O:19])[CH:17]=[CH:16][C:15](C(O)=O)=[CH:14]1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC[N:25]([CH:29](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1.[C:49]([OH:53])([CH3:52])([CH3:51])[CH3:50]>O1CCOCC1>[Si:1]([O:8][CH2:9][C:10]([N:13]1[C:18](=[O:19])[CH:17]=[CH:16][C:15]([NH:25][C:29](=[O:39])[O:53][C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:14]1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 688193341-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid

생성물 1

HCID 59843016tert-Butyl 1-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A stirred solution of 1-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid (2980 mg, 9.15 mmol), DIPEA (3198 μl, 18.3 mmol), diphenylphosphoryl azide (3.97 mL, 18.3 mmol), and t-butanol (8.60 mL, 9.15 mmol) in Dioxane (10 mL) was heated to reflux under nitrogen for 21 h. The reaction mixture was concentrated under reduced pressure and was purified on silica (80 g) eluting with 10-30% EtOAc/hexane. MS (ESI pos. ion) m/z (MH+): 397. Calc'd exact mass for C20H36N2O4Si: 396. 1H NMR (400 MHz, Chloroform-d) δ ppm −0.04 (s, 6 H) 0.81 (s, 9H) 1.49 (s, 9H) 1.63 (s, 6 H) 4.03 (s, 2 H) 5.98 (s, 1 H) 6.41 (d, J=9.54 Hz, 1 H) 7.15 (dd, J=9.54, 2.51 Hz, 1 H) 7.79 (br. s., 1 H).

후처리

  1. temperatureto reflux under nitrogen for 21 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customwas purified on silica (80 g)
  4. washeluting with 10-30% EtOAc/hexane

출처 및 근거

ORD 기록
ord-3f9d280c297d4ba4b786660218a6a263
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314087B2

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