Triethylamine → HCID 54061775, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C@H:5]([CH2:7][S:8][CH2:9][CH2:10][S:11][CH:12]([CH3:14])C)[NH2:6])[CH3:2].[C:16]([O:20][C:21](=[O:25])[CH:22](Br)[CH3:23])([CH3:19])([CH3:18])[CH3:17].[CH2:26](N(CC)CC)C>CN(P(N(C)C)(N(C)C)=O)C>[C:16]([O:20][C:21](=[O:25])[C@H:22]([CH3:23])[NH:6][C@H:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH2:7][S:8][CH2:9][CH2:10][S:11][CH2:12][CH2:14][CH3:26])([CH3:19])([CH3:18])[CH3:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In 50 ml of HMPA were dissolved 12.2 g of S-2-propylthioethyl-L-cysteine ethyl ester and 11.2 g of 2-bromopropionic acid t-butyl ester. A 7.5 ml quantity of triethylamine was added to the solution and the mixture was stirred at room temperature for 40 hours. The reaction mixture was poured into ice water and the mixture was extracted with ethyl acetate. The extract was washed with water and with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure and the residue was purified by silica gel column chromatography (a 1:3 mixture of ether and n-hexane as an eluent), giving the α-isomer of the title compound as a colorless oil from the first eluate. Yield 2.58 g.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water and with a saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated off under reduced pressure
- customthe residue was purified by silica gel column chromatography (
- additiona 1:3 mixture of ether and n-hexane as an eluent),
Sources & evidence
- ORD record
- ord-46b31e14a2bf4100bd0e5198ca81a324
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04977179
Reaction notes
Loading…