Hydrochloric Acid → N-[1(S)-benzyl-3-hydroxy-2-oxopropyl]phthalimide

HRID 440104

反応式

HRID 440104 の反応式
[C:1]1([CH2:7][C@H:8]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](C)(C)[O:25][CH:26]=C(O[Si](C)(C)C)O[Si](C)(C)C.Cl.[Cl-].[Na+]>O1CCOCC1>[CH2:7]([C@H:8]([N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])[C:9](=[O:10])[CH2:26][OH:25])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 553067(Vinyl-2-ylidenetris(oxy))tris(trimethylsilane)2 回HCID 105671973-phenyl-2(S)-phthalimidopropionyl chloride

生成物 1

HCID 10267319N-[1(S)-benzyl-3-hydroxy-2-oxopropyl]phthalimide収率 78%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

A mixture of 134 g of 3-phenyl-2(S)-phthalimidopropionyl chloride and 269.7 g of tris(trimethylsilyloxy)ethylene was stirred at 95° C. for 5 hours. A further 54 g of tris(trimethylsilyloxy)ethylene were added and the mixture was stirred at 95° C. for a further 1.5 hours. The cooled reaction mixture was then treated with 435 ml of dioxan and 174 ml of 0.6N hydrochloric acid and the resulting mixture was heated to 85° C. for 30 minutes. The cooled mixture was saturated with sodium chloride and then extracted with diethyl ether. The ethereal solution was washed with aqueous sodium bicarbonate solution and evaporated. The resulting pale yellow solid was crystallized from ethyl acetate/n-hexane to give 103 g of N-[1(S)-benzyl-3-hydroxy-2-oxopropyl]phthalimide as a white solid, MS: m/e 310 [M+H]+.

後処理

  1. stirringthe mixture was stirred at 95° C. for a further 1.5 hours
  2. customThe cooled reaction mixture
  3. temperaturethe resulting mixture was heated to 85° C. for 30 minutes
  4. extractionextracted with diethyl ether
  5. washThe ethereal solution was washed with aqueous sodium bicarbonate solution
  6. customevaporated
  7. customThe resulting pale yellow solid was crystallized from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-c03e497891c34458806f392a61a3b844
出典データセット
uspto-grants-1996_05
特許番号
US05516913

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