Triethylamine → N-[(R)-1-ethoxycarbonyl-2-heptylthioethyl]-alanine t-butyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C@H:5]([CH2:7][S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[NH2:6])[CH3:2].[C:17]([O:21][C:22](=[O:26])[CH:23](Br)[CH3:24])([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>CN(P(N(C)C)(N(C)C)=O)C>[C:17]([O:21][C:22](=[O:26])[C@H:23]([CH3:24])[NH:6][C@H:5]([C:4]([O:3][CH2:1][CH3:2])=[O:16])[CH2:7][S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([CH3:20])([CH3:19])[CH3:18]Participants
5
Procedure
In 20 ml of HMPA were dissolved 5.9 g of S-heptyl-L-cysteine ethyl ester and 5.5 g of 2-bromopropionic acid t-butyl ester. A 3.4 ml quantity of triethylamine was added to the solution. The mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The extract was sufficiently washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was separated and purified by silica gel column chromatography (a 1:3 mixture of ether and n-hexane as an eluent), producing the α-isomer of the title compound as a colorless oil from the first eluate. Yield 2.8 g.
Workup
- extractionfollowed by extraction with ethyl acetate
- washThe extract was sufficiently washed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was separated
- custompurified by silica gel column chromatography (
- additiona 1:3 mixture of ether and n-hexane as an eluent),
Sources & evidence
- ORD record
- ord-38a6d986becf47b1ae07f3b35b88d9d0
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04886813
Reaction notes
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