Electric Literature of 680-65-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 680-65-9, name is Diethyl difluoromalonate, This compound has unique chemical properties. The synthetic route is as follows.
EXAMPLE 152. Preparation of 4-((lR,3aS,5aR,5bR,7aR,llaS,llbR,13aR,13bR)-3a ((3-(2-(dimethylamino)ethylamino)-2,2-difluoro-3-oxopropanamido)methyl)- 5a,5b,8,8, 11 a-pentamethyl- 1 -(prop- 1 -en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,ll,lla,llb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoic acid. Step 1: Preparation of the C28 reversed amide To a solution of tert-butyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- (aminomethyl)-5a,5b,8,8, 11 a-pentamethyl-1 -(prop- 1 -en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate (200 mg, 0.333 mmol) in methanol (5 ml) and 1,4-dioxane (5 ml) was added diethyl 2,2-difluoromalonate (654 mg, 3.33 mmol). The resulting solution was stirred at rt for 6 days. The reaction mixture was concentrated in vacuo. The crude product was purified by Biotage (Thomson 25 g silica gel column; 4: 1 Hex/EtOAc) to give 116 mg (47 %) of product. MS: m/e 736.6 (MH+), 2.86 min (method 2). ? NMR (400 MHz, CHLOROFORM-d) delta ppm 0.93 (s, 6 H) 0.99 (s, 3 H) 1.02 (s, 3 H) 1.13 (s, 3 H) 1.60 (s, 9 H) 1.71 (s, 3 H) 0.85 – 1.83 (20 H) 1.98 – 2.10 (m, 1 H) 2.10 (dd, J=17.07, 6.27 Hz, 1 H) 2.49 (td, J=l 1.04, 5.27 Hz, 1 H) 3.16 (dd, J=13.55, 6.27 Hz, 1 H) 3.65 (dd, J=14.43, 7.15 Hz, 1 H) 3.95 (s, 3 H) 4.61 – 4.65 (m, 1 H) 4.73 (d, J=1.76 Hz, 1 H) 5.28 (dd, J=6.15, 1.63 Hz, 1 H) 6.28 (t, J=7.03 Hz, 1 H) 7.18 (d, J=8.53 Hz, 2 H) 7.89 (d, J=8.28 Hz, 2 H). iyF NMR (376 MHz, CHLOROFORM-d) delta ppm -112.49 (s, 2 F).
The chemical industry reduces the impact on the environment during synthesis Diethyl difluoromalonate. I believe this compound will play a more active role in future production and life.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; REGUEIRO-REN, Alicia; SWIDORSKI, Jacob; SIT, Sing-Yuen; CHEN, Yan; CHEN, Jie; MEANWELL, Nicholas A.; LIU, Zheng; WO2012/106188; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics