Hydrochloric Acid → N-[1(S)-benzyl-3-hydroxy-2-oxopropyl]phthalimide
Reaction equation
[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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
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]+.
Workup
- stirringthe mixture was stirred at 95° C. for a further 1.5 hours
- customThe cooled reaction mixture
- temperaturethe resulting mixture was heated to 85° C. for 30 minutes
- extractionextracted with diethyl ether
- washThe ethereal solution was washed with aqueous sodium bicarbonate solution
- customevaporated
- customThe resulting pale yellow solid was crystallized from ethyl acetate/n-hexane
Sources & evidence
- ORD record
- ord-b79cc8c7dcdb49b29f92959c90a943f2
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05580999
Reaction notes
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