With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.30379-58-9, name is Benzyl 2-hydroxyacetate, molecular formula is C9H10O3, molecular weight is 166.17, as common compound, the synthetic route is as follows.Quality Control of Benzyl 2-hydroxyacetate
2-(Fluorenylmethoxycarbonyl)hydroxyacetic acid benzyl ester (657). To a solution of benzyl glycolate (6.0 g, 36.1 mmol) in CH2Cl2, cooled via ice-water bath, was added fluorenylmethoxy chloroformate (14 g, 1.5 equiv.) then diisopropylethylamine (9 mLs, 1.5 equiv.). After 1 hour, reaction mixture was poured into a saturated aqueaous solution of ammonium chloride and extracted with CH2Cl2, dried over Na2SO4 then concentrated in vacuo. The product was triturated from MeOH to obtain 2.2 g of 657 as a first crop of white solid. 2-(Fluorenylmethoxycarbonate) acetic acid (658). To a solution of 657 (2.2 g, 5.93 mmol) in tetrahydrofuran was added 5% Pd/C (220 mg). The resulting suspension was vigorously stirred under hydrogen atmosphere. After 90 min, the reaction mixture was filterred through Celite. The filtrate was poured into saturated aqueous NaHCO3 and washed twice with EtOAc. The aqueous layer was then acidified and the product extracted twice with CH2Cl2, dried over Na2SO4 and concentrated in vacuo to afford 1.46 g (88%) of 658 as a white solid. 2-(Fluorenylmethoxycarbonate) acetyl chloride (659), was prepared from 658 by the method used to prepare 643 to afford 659 as a crude product. (3S)-3-[(3S)-2-Oxo-3-(3,5-dichloro-4-hydroxybenzoyl)amino-5-(2-fluorenylmethoxycarbonate)acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetylamino]4-oxo-butyric acid tert-butyl ester semicarbazone (660), was synthesised from 600b, using 659, by methods used to prepare 604d from 600b to afford 453 mg of 660. (3S)-3-[(3S)-2-Oxo-3-(3,5-dichloro-4-hydroxybenzoyl)amino-5-(2-hydroxy)acetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetylamino]4-oxo-butyric acid tert-butyl ester semicarbazone (661). A solution of 660 (423 mg) in MeOH:Et2NH (1:1, v/v) was stirred at ambient temperature.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,30379-58-9, Benzyl 2-hydroxyacetate, and friends who are interested can also refer to it.
Reference:
Patent; Vertex Pharmaceuticals Incorporated; US6204261; (2001); B1;,
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