* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Journal of the American Chemical Society, 1995, vol. 117, # 49, p. 12342 - 12343
[2] Journal of the American Chemical Society, 1995, vol. 117, # 49, p. 12342 - 12343
[3] Tetrahedron Letters, 1995, vol. 36, # 37, p. 6627 - 6630
[4] Tetrahedron, 2001, vol. 57, # 15, p. 2965 - 2972
{2-[3-(2,6-difluoro-benzyl)-5-(2-fluoro-3-methoxy-phenyl)-4-methyl-2,6-dioxo-3,6-dihydro-2<i>H</i>-pyrimidin-1-yl]-1-phenyl-ethyl}-methyl-carbamic acid <i>tert</i>-butyl ester[ No CAS ]
Original PG01 is a racemic mixture. To determine which enantiomer was contributing to the high nM potency, both enantiomers of PG01 were synthesized and their activity compared to the racemic mixture. The enantiomers were synthesized from their corresponding D/L-amino acids via the method <n="56"/>used to synthesize M1 .1 . The optical rotations of M2.1 and M2.2 were -4.09 and +4.07, respectively. This indicated that the products were chiral.
Original PG01 is a racemic mixture. To determine which enantiomer was contributing to the high nM potency, both enantiomers of PG01 were synthesized and their activity compared to the racemic mixture. The enantiomers were synthesized from their corresponding D/L-amino acids via the method <n="56"/>used to synthesize M1 .1 . The optical rotations of M2.1 and M2.2 were -4.09 and +4.07, respectively. This indicated that the products were chiral.
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 4h;
Example 7 Preparation of (R)-tert-butyl 2-(isoquinolin-6-ylamino)-2-oxo-1-phenylethyl(methyl)carbamate (E7) To (R)-2-(tert-butoxycarbonyl(methyl)amino)-2-phenylacetate (E6) in DMF was added EDC, DMAP and <strong>[23687-26-5]6-aminoisoquinoline</strong>. This mixture was stirred for 4 hours and the reaction was washed with NaHCO3 (sat), extracted with EtOAc, dried (Na2SO4), filtered and evaporated. Column chromatography (SiO2, Hexanes/EtOAc) gave pure (R)-tert-butyl 2-(isoquinolin-6-ylamino)-2-oxo-1-phenylethyl(methyl)carbamate (E7).
Example 6 Preparation of (R)-2-(tert-butoxycarbonyl(methyl)amino)-2-phenylacetate (E6) To (R)-methyl 2-(tert-butoxycarbonyl(methyl)amino)-2-phenylacetate (E5) in THF/H2O/MeOH at 0 C. was added LiOH.H2O and solution was allowed to warm and stir at room temperature for 4 hours. The mixture was acidified with HCl to pH 3-4 and extracted with EtOAc, dried (Na2SO4), filtered and evaporated to give (R)-2-(tert-butoxycarbonyl(methyl)amino)-2-phenylacetate (E6).
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