Citric Acid → HCID 11360847, compound
Reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH:11]([CH3:13])[CH3:12])[C:9]=1[OH:10])[CH3:3].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:35][CH2:36][CH2:37][N:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1.[C:43](O)(=[O:54])[CH2:44][C:45](CC(O)=O)([C:47](O)=[O:48])O>C1COCC1.C(Cl)Cl>[CH:11]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:2]([CH3:1])[CH3:3])[C:9]=1[O:10][C:43](=[O:54])[CH2:44][CH2:45][C:47]([NH:35][CH2:36][CH2:37][N:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1)=[O:48])([CH3:13])[CH3:12]Participants
7
Procedure
To a solution of propofol hemisuccinate (2.0 g, 7.2 mmol) in THF—CH2Cl2 (1:1, 60 mL) was added EDCI (1.72 g, 9 mmol) followed by HOBt (1.37 g, 9 mmol). The reaction mixture was stirred at ambient temperature for 15 min and 1-(2-aminoethyl)pyrrolidine (0.912 g, 8 mmol) was added and stirring was maintained overnight. 10% aqueous citric acid (50 ml) was added and the mixture was extracted with CH2Cl2 (100 ml×2). The organic layer was washed with brine and dried over anhydrous MgSO4. The solvent was removed and the product was purified by silica gel column chromatography using acetone with 1% Et3N. Removal of the solvent gave the product as an oil. Yield: 2.47 gram (92%)
Workup
- stirringstirring
- temperaturewas maintained overnight
- extractionthe mixture was extracted with CH2Cl2 (100 ml×2)
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous MgSO4
- customThe solvent was removed
- customthe product was purified by silica gel column chromatography
- customRemoval of the solvent
Sources & evidence
- ORD record
- ord-bd1938ba94b54f34817eb2be1295f17e
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691904B2
Reaction notes
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