Reaction equation
[NH2:1][C@H](C(O)=O)CCCC.C(N(CC)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.Cl.[CH2:35]([NH:39][C:40](=[O:53])[CH:41]([CH2:51][CH3:52])[CH2:42][C@H:43]([OH:50])[C@@H:44](N)[CH2:45][CH:46]([CH3:48])[CH3:47])[CH:36]([CH3:38])[CH3:37]>CN(C=O)C.C(OCC)(=O)C>[CH2:35]([NH:39][C:40](=[O:53])[C:41]([NH2:1])([CH2:51][CH3:52])[CH2:42][CH:43]([OH:50])[CH2:44][CH2:45][CH:46]([CH3:48])[CH3:47])[CH:36]([CH3:38])[CH3:37]Participants
Conditions
- Temperature
- -15 °C
Procedure
20.7 mg of L-N-[(2R or S)-5-ethylthio-2-(naphthylmethyl)pentanoyl]norleucine was dissolved in 0.5 ml of dry DMF. Then, 27.4 μl of triethylamine, 12.9 μl of DPPA and 20 mg of (2RS,4S,5S)-5-amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide monohydrochloride was added thereto under stirring at -15° C. The mixture was stirred at the same temperature for one hour and then at 5° C. overnight. The reaction solution was diluted with 20 ml of ethyl acetate, washed with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=50/1) to obtain 16.9 mg of (2RS,4S,5S)-5-{L-N-[(2R or S)-5-ethylthio-2-(1-naphthylmethyl)pentanoyl]norleucyl}amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide as colorless solid.
Workup
- stirringThe mixture was stirred at the same temperature for one hour
- customat 5° C.
- customovernight
- washwashed with water and with a saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous sodium sulfate
- distillationThen, the solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (chloroform/methanol=50/1)
Sources & evidence
- ORD record
- ord-b6084522f7014ffaa529682d1bee6a84
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05481036
Linked notes
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