In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Chloromethyl isobutyrate, other downstream synthetic routes, hurry up and to see.
Application of 61644-18-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 61644-18-6, name is Chloromethyl isobutyrate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
To a stirred solution of (S)-1 -(((3-cyanopyridin-2-yl)oxy)methyl)-4- ((1 R,3aS,5aR,5bR,7aR,1 1 aS,1 1 bR,13aR,13bR)-3a-((2-((1 s,4R)-1 -hydroxy-4- (methylsulfonyl)cyclohexyl)ethyl)amino)-5a,5b,8,8, 1 1 a-pentamethyl-1 -(prop-1 -en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,1 1 ,1 1 a,1 1 b,12,13,13a,13b-octadecahydro-1 H- cyclopenta[a]chrysen-9-yl)cyclohex-3-ene-1 -carboxylic acid (200 mg, 0.230 mmol) and chloromethyl isobutyrate (62.8 mg, 0.460 mmol) in DMF (5.0 ml_) were added potassium carbonate (159 mg, 1 .149 mmol) followed by sodium iodide (6.89 mg, 0.046 mmol) at 0 C under Nitrogen atmosphere. The reaction mixture was allowed to warm to 27 C and stirred for 16 hr. The progress of the reaction was monitored by TLC (Si02, 5% MeOH/DCM, Rf = 0.4, KMn04-active). The reaction mixture was quenched with ice water (50 ml_) and extracted with EtOAc (2 c 30 ml_). The combined organic layers were washed with brine (50 ml_), dried over Na2S04, filtered and concentrated under reduced pressure to give the crude residue as sticky oil. The crude compound was triturated with chilled n-pentane (3 x 10 ml_) filtered and dried under high vacuum to afford (isobutyryloxy)methyl (S)-1 -(((3-cyanopyridin-2-yl)oxy)methyl)-4- ((1 R,3aS,5aR,5bR,7aR,1 1 aS,1 1 bR,13aR,13bR)-3a-((2-((1 s,4R)-1 -hydroxy-4- (methylsulfonyl)cyclohexyl)ethyl)amino)-5a,5b,8,8, 1 1 a-pentamethyl-1 -(prop-1 -en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,1 1 ,1 1 a,1 1 b,12,13,13a,13b-octadecahydro-1 H- cyclopenta[a]chrysen-9-yl)cyclohex-3-ene-1 -carboxylate (93 mg, Yield: 40%, white solid. NMR (400 MHz, CDCI3) d = 8.32 (dd, J = 2.0, 5.0 Hz, 1 H), 7.86 (dd, J = 2.0, 7.5 Hz, 1 H), 6.98 (dd, J = 5.0, 7.6 Hz, 1 H), 5.81-5.77 (m, 2H), 5.36-5.33 (m, 1 H), 5.19-5.17 (m, 1 H), 4.74-4.71 (m, 1 H), 4.61 -4.55 (m, 3H), 2.84-2.64 (m, 7H), 2.57-2.50 (m, 1 H), 2.25- 1 .82 (m, 12H), 1 .72-1 .38 (m, 22H), 1 .32-1 .22 (m, 6H), 1 .13 (d, J = 7.0 Hz, 6H), 1 .07-1 .01 (m, 6H), 0.98-0.94 (m, 6H), 0.93-0.88 (m, 3H), 0.86-0.82 (m, 3H). LCMS: RT = 7.1 1 mins, (M+H) = 970.4, Purity = 97%, HPLC Purity = 96%, Chiral HPLC Purity = 94%.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Chloromethyl isobutyrate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; KADOW, John F.; NAIDU, B. Narasimhulu; (61 pag.)WO2019/207460; (2019); A1;,
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