A New Method for the Preparation of α-Bromoesters

Glucose Transport-Enhancing and Hypoglycemic Activity of 2-Methyl-2-phenoxy-3-phenylpropanoic Acids

“…Modification of the 4-isopropyl group in the phenoxy part of 7 led to analogs (15)(16)(17)(18) that generally did not exhibit hypoglycemic activity at 25 mg/kg. Similarly, shortening (19) the distance between the R-carbon and the phenyl ring of the 3-phenylpropanoic acids by one C atom decreased the hypoglycemic activity, while increasing this distance by four (21), but not one (20), C atoms retained hypoglycemic activity. Although there was some correlation between the ability of these compounds to acutely enhance 2-deoxyglucose uptake in 3T3-L1 adipocytes in vitro, we surprisingly found several compounds which showed activity in one of, but not both, the in vitro and in vivo screens (1,2,5,11,19).…”

“…4-(4-Chlorophenyl)-2-(4-isopropylphenoxy)butanoic Acid (20). A 410 mg (1.34 mmol) sample of 2-bromo-4-(4-chlorophenyl)butyrate, obtained by the method of Dice and Bowden by alkylation of diethyl malonate with 2-(4-chlorophenyl)ethyl chloride in the presence of NaOEt in EtOH followed by monosaponification with KOH to the potassium salt followed by treatment with Br 2 in CCl 4 , was converted with 53 mg of 60% NaH and 182 mg of 4-isopropylphenol as described in General Method A to 200 mg (41%) of ethyl 4-(4-chlorophenyl)-2-(4-isopropylphenoxy)butyrate: MS (EI) m / e 360 (M); NMR (CDCl 3 ) δ 1.2−1.3 (m, 9H, Me), 2.1−2.4 (m, 2H, CH 2 ), 2.6−2.9 (m, 3H, CH, benzylic CH 2 ), 4.15 (q, 2H, O-CH 2 ), 4.5 (dd, 1H, (α-H), 6.8 (d, 2H, H-2), 7.15 (m, 4H, aromatic H‘), 7.2 (d, 2H, H-3).…”

The Degradation Of Carboxylic Acid Salts By Means Of Halogen - The Hunsdiecker Reaction

“…The alkali metal salts (sodium and potassium) have found limited application (15,42,51,59,71,73,74,101), but there seems to be no reason to prefer them to the silver salts. The former usually are water-soluble and hence difficult to isolate; frequently they are hygroscopic.…”

Nonnucleoside HIV-1 Reverse Transcriptase Inhibitors: Part I. Synthesis and Structure-Activity Relationship of 1-Alkoxymethyl-5-alkyl-6-naphthylmethyl Uracils as HEPT Analogues

“…The synthesis method of the b-series compounds is similar to that of their a-counterparts except for the different raw material. butyrates 5a-d were prepared upon reaction of 1-naphthylacetonitrile with activated zinc dust and ethyl 2-bromoalkanoates 4a-d 18) using an improved method of the Blaise Reaction 19,20) described previously. 21,22) The so formed 3-oxo esters 5a-d were converted into a 5-alkyl-6-(1-naphthylmethyl)-2-thiouracil 6a-d by reaction with thiourea in the presence of NaOEt.…”