Sodium Hydroxide → HCID 10607088, compound

Participants

Reaction Conditions

Reaction Steps

A liquid broth (45 ml) comprising 3 g of yeast extract, 6.5 g of diammonium hydrogen phosphate, 1 g of potassium dihydrogen-phosphate, 0.8 g of magnesium sulfate heptahydrate, 60 mg of zinc sulfate heptahydrate, 90 mg of iron sulfate heptahydrate, 5 mg of copper sulfate pentahydrate, 10 mg of manganese sulfate tetrahydrate and 100 mg of sodium chloride, per 900 milliliters, and one drop of Adekanol were placed in a 500-ml Sakaguchi flask and sterilized, 5 ml of a sterilized 40% aqueous solution of glucose was added, and the whole was aseptically inoculated with 1 ml of the culture of Candida maris IFO 10003 as obtained by the culture method described in Example 1, and shake culture was carried out at 30° C. for 24 hours. The resulting culture was used as a seed yeast. A 5-liter jar fermenter was charged with 2.25 liters of the liquid broth having the above composition and 5 drops of Adekanol and, after sterilization, 250 ml of a sterilized 40% aqueous solution of glucose was added, and the whole was aseptically inoculated with 50 ml of the seed. Cultivation was carried out under the following conditions for 40 hours: cultivation temperature 30° C., rate of stirring 350 rpm, aeration 0.75 L/min. When, during cultivation, the pH was found to have become lower than 5.5, the pH was adjusted to 5.5 by adding 5 N aqueous sodium hydroxide. After cultivation, 2 L of the culture containing microbial cells, 10 g of 5-acetylfuro[2,3-c]pyridine and 60 g of glucose were placed in a 5-liter jar fermenter, and the reduction reaction was carried out at 30° C. with stirring for 22.5 hours. During the reaction, the pH of the reaction mixture was maintained at pH 6 using 5 N aqueous sodium hydroxide. At 4.5 hours and 7.5 hours after the start of the reaction, 60 g of glucose and 80 g of glucose were added, respectively. After completion of the reaction, the reaction mixture was extracted with 1 liter of ethyl acetate and the aqueous phase was further extracted with 1 liter of ethyl acetate. The organic phases were combined and dehydrated over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. To the residue were added 30 ml of ethyl acetate and 500 mg of active carbon, and the mixture was stirred at room temperature for 2 hours. The active carbon was removed by filtration and the solvent was then distilled off under reduced pressure. The residue was crystallized from a mixed solution composed of ethyl acetate and methylcyclohexane to give 8.1 g of 5-(1-(R)-hydroxyethyl)furo[2,3-c]pyridine as white solid. Yield: 81%, optical purity: 98.7% e.e., melting point: 59.5 to 60.5° C., specific rotation [α]D20=+37.0° (CHCl3, c=0.56). 1H-NMR δ (CDCl3): 1.56 (3H, d, J=6.35 Hz), 4.12 (1H, s), 5.00 (1H, q, J=6.35 Hz), 6.80 (1H, d, J=1.95 Hz), 7.54 (1H, s), 7.77 (1H, d, J=1.95 Hz), 8.80 (1H, s).

Provenance & Evidence