反応 #160997

反応方程式

(2S,3S)-3-amino-1-chloro-2-hydroxy-4-phenylbutane hydrochloride

(2S,3S)-3-amino-1-chloro-2-hydroxy-4-phenylbutane

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

1,1′-carbonyldiimidazole

→

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-N-[(1S,2R)-3-chloro-1-benzyl-2-hydroxypropyl]carbamate

溶媒

THF

ethyl acetate

THF

反応条件

後処理

1. 1
   その他After completion of reaction the solution
2. 2
   温度was cooled
3. 3
   洗浄washed with water (40 mL), diluted hydrochloric acid (40 ml), 5% aqueous sodium hydrogen carbonate (40 mL) and water (50 mL)
4. 4
   乾燥The solution was dried over sodium sulfate
5. 5
   その他evaporated to dryness

実験手順

1,1′-carbonyldiimidazole (162.15 g, 1 mol) was added to THF (0.5 L), following by solution of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol (135.2 g, 1.04 mol) in 0.3 L of THF and the mixture was stirred for a further hour. (2S,3S)-3-amino-1-chloro-2-hydroxy-4-phenylbutane hydrochloride (229 g, 0.97 mol) was added and the mixture heated at 55-60° C. approximately 5-6 hours under TLC control (for complete disappearance of (2S,3S)-3-amino-1-chloro-2-hydroxy-4-phenylbutane). After completion of reaction the solution was cooled and transformed to the next step. For the preparation of analytical sample, 10 ml of solution was diluted with 50 ml of ethyl acetate, washed with water (40 mL), diluted hydrochloric acid (40 ml), 5% aqueous sodium hydrogen carbonate (40 mL) and water (50 mL). The solution was dried over sodium sulfate and evaporated to dryness. MS: m/z 356 (MH+). NMR spectrum corresponded to the structure of the desired product.

出典