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

HRID 1878720ノート

反応式

HRID 1878720 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3f9d280c297d4ba4b786660218a6a263
出典データセット
uspto-grants-2012_11
特許番号
US08314087B2

反応ノート

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