Ethylamine → (S)-2-(Cbz-amino)-N-ethylpropanamide
Reaction equation
[CH2:1]([N:3]1CCCCC1)[CH3:2].[CH2:9]([O:16][C:17]([NH:19][C@H:20]([C:22]([OH:24])=O)[CH3:21])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.ClC(OC(CC)C)=O.C(N)C>O1CCCC1>[CH2:1]([NH:3][C:22](=[O:24])[C@H:20]([CH3:21])[NH:19][C:17]([O:16][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:18])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -6 °C
Procedure
14 ml. of N-ethyl piperidine was added to a solution of 23.3 grams of benzyloxycarbonyl alanine in 100 ml. of tetrahydrofuran and, after cooling to -10 degrees C., 14 ml. of sec. butyl chlorformate was added. Next, the mixture was stirred for 8 minutes and cooled to -6 degrees C. Then 30 ml. of a 4.1 solution of ethylamine in tetrahydrofuran was added. After 30 minutes of stirring at 0 degrees C. and 2 hours of stirring at room temperature, the reaction solution was evaporated, gradually shaken with a 5% solution of sodium hydrogen carbonate, with water, dried with anhydrous sodium carbonate, and evaporated. The evaporation residue was crystallized from ethyl acetate (30 ml.) and petroleum ether. 18.1 g of a product having a melting point of 116 to 117 degrees C. was obtained.
Workup
- stirringAfter 30 minutes of stirring at 0 degrees C
- stirringand 2 hours of stirring at room temperature
- customthe reaction solution was evaporated
- stirringgradually shaken with a 5% solution of sodium hydrogen carbonate, with water
- dry with materialdried with anhydrous sodium carbonate
- customevaporated
- customThe evaporation residue was crystallized from ethyl acetate (30 ml.) and petroleum ether
- customwas obtained
Sources & evidence
- ORD record
- ord-b62132507a9c4e72a92a053969d44aea
- Source dataset
- uspto-grants-1985_11
- Patent number
- US04554100
Reaction notes
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