Trifluoroacetic acid → HCID 54132879, compound
Reaction equation
[CH3:1][N:2]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:3](=[O:31])[C:4]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23]C(OC(C)(C)C)=O)=[CH:19][CH:18]=1)=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][N:2]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:3](=[O:31])[C:4]([CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=1)=[CH:5][C:6]1[CH:7]=[CH:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
10 g of N-methyl-N-octadecyl-α-(4-t-butoxycarbonylaminophenoxy)methyl-4-nitrocinnamic acid amide was dissolved in 50 ml of chloroform. The mixture was then cooled to a temperature of 0° C. or lower. 12 ml of trifluoroacetic acid wa gradually added dropwise to the mixture. The mixture was then stirred at room temperature for 10 hours. After the reaction was completed, the reaction mixture was neutralized with an aqueous solution of sodium bicarbonate. The neutralized mixture was then extracted with ethyl acetate. The extract was subjected to silica gel flash column chromatography. The desired substance was then obtained from a fraction extracted from a 1:1 mixture of ethyl acetate and hexane. (Yield: 5.4 g (63%))
Workup
- extractionThe neutralized mixture was then extracted with ethyl acetate
- customThe desired substance was then obtained from a fraction
- extractionextracted from a 1:1 mixture of ethyl acetate and hexane
Sources & evidence
- ORD record
- ord-f0c59c565ac943068aab11aa5ac9e62d
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04994363
Reaction notes
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