Hexanoyl chloride → HCID 86754010, compound
Reaction equation
Cl.Cl.[CH3:3][O:4][C:5](=[O:18])[CH:6]([NH2:17])[CH2:7][S:8][S:9][CH2:10][CH:11]([NH2:16])[C:12]([O:14][CH3:15])=[O:13].C(N([CH:25]([CH3:27])[CH3:26])C(C)C)C.[C:28](Cl)(=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>O1CCCC1>[CH3:3][O:4][C:5](=[O:18])[C@@H:6]([NH:17][C:5](=[O:4])[CH2:6][CH2:7][CH2:27][CH2:25][CH3:26])[CH2:7][S:8][S:9][CH2:10][C@H:11]([NH:16][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:12]([O:14][CH3:15])=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A suspension of 1 equiv. 3,3'-dithiobis(2-aminopropionic acid) dimethylester dihydrochloride in tetrahydrofuran (white slurry) was stirred and cooled to 0° C. To the reaction mixture was added 4 equiv. of N-ethyldiiso-propylamine and 2.2 equiv. of hexanoylchloride. The mixture was stirred for 4 hrs on an ice bath and the white precipitate of N-ethyldiisopropylammonium chloride was filtered off. The solvent was removed by evaporation under reduced pressure and the crude product was redissolved in dichlormethane. After washing with water, the organic phase was dried over sodium sulphate. Filtration and evaporation of the solvent gave crude (R,R)-N,N'-dihexanoyl-3,3'-dithiobis(2-aminopropionic acid) dimethylester, which was recrystallized from methanol/water and triturated with diethylether.
Workup
- additionA suspension of 1 equiv
- filtrationthe white precipitate of N-ethyldiisopropylammonium chloride was filtered off
- customThe solvent was removed by evaporation under reduced pressure
- dissolutionthe crude product was redissolved in dichlormethane
- washAfter washing with water
- dry with materialthe organic phase was dried over sodium sulphate
- filtrationFiltration and evaporation of the solvent
Sources & evidence
- ORD record
- ord-481e5dfe43ed4ef7a25e114ea048e016
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05889050
Reaction notes
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