Hydrochloric Acid → (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]azetidin-2-one

HRID 648689ノート

反応式

HRID 648689 の反応式
[Si]([N:8]1[C@H:11]([CH2:12][C:13](=[O:28])[CH2:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[C@@H:10]([C@H:29]([O:31][Si](C(C)(C)C)(C)C)[CH3:30])[C:9]1=[O:39])(C(C)(C)C)(C)C.Cl>CO.O.C(OCC)(=O)C>[OH:31][C@@H:29]([C@@H:10]1[C@@H:11]([CH2:12][C:13](=[O:28])[CH2:14][C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[O:16])[NH:8][C:9]1=[O:39])[CH3:30]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 13018175(3S,4R)-1-(t-butyldimethylsilyl)3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]azetidin-2-one

生成物 1

HCID 13018177(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]azetidin-2-one

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
0 °C

実験手順

(3S,4R)-1-(t-butyldimethylsilyl)3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]azetidin-2-one (7.9 mmol) is dissolved in 160 ml of 9:1 (v/v) methanol-water and cooled to 0° C. Concentrated hydrochloric acid (2.75 ml) is added and the resulting solution is stirred at 0° C. for 15 min., then allowed to warm to room temperature. The solution is stirred at room temperature for 2.5 hrs, then diluted with ethyl acetate (200 ml) and washed with water, saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo to yield (3S,4R)-3-[(R)1-hydroxyethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]-azetidin-2-one.

後処理

  1. temperatureto warm to room temperature
  2. stirringThe solution is stirred at room temperature for 2.5 hrs
  3. washwashed with water, saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a5eea580cd2a471ab38bca975cf7f36b
出典データセット
uspto-grants-1988_04
特許番号
US04736025

反応ノート

読み込み中…