Triethylamine → HCID 70386402, compound
Reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:25])[C@H:12]([CH2:14][S:15][CH2:16][C:17](=[O:24])[NH:18][CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[NH2:13])[CH3:9].[C:26]([O:30][C:31](=[O:35])[CH:32](Br)[CH3:33])([CH3:29])([CH3:28])[CH3:27]>CN(P(N(C)C)(N(C)C)=O)C>[C:26]([O:30][C:31](=[O:35])[C@H:32]([CH3:33])[NH:13][C@H:12]([C:11]([O:10][CH2:8][CH3:9])=[O:25])[CH2:14][S:15][CH2:16][C:17](=[O:24])[NH:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1)([CH3:29])([CH3:28])[CH3:27]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A 2.8 ml of triethylamine was added to a solution of 5.5 g of S-cyclopentylcarbamoylmethyl-L-cysteine ethyl ester and 4.2 g of 2-bromopropionic acid t-butyl ester in 10 ml of HMPA. The mixture was stirred at room temperature for 30 hours. The reaction mixture was poured into ice water and the mixture was extracted with ethyl acetate. The extract was sufficiently washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a 10:1 mixture of ether and n-hexane as an eluent), producing the α-isomer of the title compound from the first eluate as a colorless oil. Yield 1.36 g.
Workup
- extractionthe mixture was extracted 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 purified by silica gel column chromatography (
- additiona 10:1 mixture of ether and n-hexane as an eluent),
Sources & evidence
- ORD record
- ord-6fa3584dc3f14fb598ea468e8d250fce
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04886813
Reaction notes
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