L-Hydroxyproline → trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

6.55 g of trans-4-hydroxy-L-proline and 7.5 ml of triethylamine were dissolved in 15 ml of water, and a solution of 15.95 g of S-p-nitrobenzyloxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine in 35 ml of dioxane was added thereto dropwise. The resulting mixture was stirred at room temperature for 1.5 hours and allowed to stand overnight. To the reaction mixture was added 30 ml of a 2N sodium hydroxide aqueous solution under ice-cooling, and the resulting mixture was extracted with diethyl ether. The ethereal layer was washed with 20 ml of a 1N sodium hydroxide aqueous solution and combined with the alkaline aqueous layer. The combined mixture was made acidic with 100 ml of a 2N hydrochloric acid aqueous solution and extracted with ethyl acetate. The ethyl acetate layer was washed with a 2N aqueous solution of hydrochloric acid, dried over sodium sulfate and distilled off to remove the solvent. The resulting crude crystals were washed with warm ethyl acetate to obtain trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline.

1. waitto stand overnight
2. temperaturecooling
3. extractionthe resulting mixture was extracted with diethyl ether
4. washThe ethereal layer was washed with 20 ml of a 1N sodium hydroxide aqueous solution
5. extractionextracted with ethyl acetate
6. washThe ethyl acetate layer was washed with a 2N aqueous solution of hydrochloric acid
7. dry with materialdried over sodium sulfate
8. distillationdistilled off
9. customto remove the solvent
10. washThe resulting crude crystals were washed with warm ethyl acetate

ORDレコード

ord-06bcd1a3722e40788de70f24251a5d72

出典データセット

uspto-grants-1990_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04933333