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

HRID 1878720Notes

Reaction equation

HRID 1878720 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3f9d280c297d4ba4b786660218a6a263
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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