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

HRID 1080505

반응식

HRID 1080505 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
95 °C

실험 절차

A mixture of 134 g of 3-phenyl-2(S)-phthalimido-propionyl 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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-b79cc8c7dcdb49b29f92959c90a943f2
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05580999

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