2-tert-Butoxycarbonylamino-6-[9-(tert-butyl-diphenyl-silanyloxy)-nonyl]-4-(3- hydroxy-propyl)-1,6

   -dihydro-pyrimidine-5-carboxylic acid methyl ester (55).

 

    Add 54 (1.0 g, 2.8 mmol, 4.0 equiv) and Grubbs Catalyst, 2nd Generation
Needed for Alkene Metathesis, or G2, (0.014 g, 0.02 mmol, .03

    equiv) to a solution of 53 (0.300 g, 0.68 mmol, 1.0 equiv) in CH2Cl2 (2.0 mL). The solution was stirred at 45

    ˚C for 15 h. The solution was then purified through column chromatography
Used to purify product based on differences in polarity (7:2:1 Hex/Benzene/EA) to obtain

    S13
Product of Alkene Metathesis (0.340 g, 73%). S13 (0.180 g, 0.20 mmol, 1.0 equiv) was dissolved into CH2Cl2/MeOH (1:6) (7.0 mL).

    AcOH
Used to facilitate deprotection mechanisms (0.030 mL) and 10% Pd(OH)2/C
Pearlman's Catalyst (100 mg) was added to the reaction mixture. The solution was degassedDegasification is the removal of dissolved gasses from liquids

    using nitrogen gas. A balloon of H2H2 is used for hydrogenation and deprotection mechanisms was inserted, as a final step. The reaction mixture was then stirred for 48

    h. The reaction mixture was filtered through celite
Celite is used to aid filtration, by allowing for the recovery of small products that would otherwise pass through or clog filter paper. and concentrated in vacuoInvolves seperation of solid product in a mixture from liquid impurities by using a vacuum to evaporate the volatile liquid , then purified by column

    chromatography (1:1 Hex/EA) to obtain 55
Reaction Product (55) (0.132 g, 90%) as a clear oil. Rf = 0.15 (1:1 Hex/EA); 1H NMR (500

    MHz, CD3OD) δ 7.65 (m, 4H), 7.45- 7.33 (m, 6H), 4.38 (dd, J = 6.9, 4.7 Hz, 1H), 3.71 (s, 3H), 3.66 (t, J = 6.5

    Hz, 2H), 3.60 (t, J = 6.5 Hz, 2H), 2.84 (m, 1H), 2.73 (m, 1H), 1.80 (m, 2H), 1.66-1.49 (m, 3H), 1.46 (s, 9H),

    1.43-1.21 (m, 10H), 1.03 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 164.9, 155.2, 152.5, 151.2, 135.8, 134.3,

    129.7, 127.8, 113.9, 86.9, 64.2, 60.7, 52.4, 51.0, 36.5, 32.8, 30.9, 29.7, 29.3, 28.1, 27.5, 27.0, 26.9, 26.0,

    25.9, 24.4, 19.4; FTIR (neat film) 3314, 2947, 2853, 1698, 1640, 1612, 1532, 1514, 1392, 1149; HRMS (ESI)+

    m/z calcd for C39H60N3O6Si [M+H]+ 694.4251, found 694.4253.

 

 

 

 

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