4-Methylmorpholine → HCID 178472555, compound
Reaction equation
[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:20][C@H:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:28])[NH2:27].Cl.Cl.CN1CCOCC1.C1CCC(N=C=NC2CCCCC2)CC1>>[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7]([NH:20][C@H:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:27])[NH2:28])=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Z-Leu-OH 172.5 g and H-Arg-OEt.2HCl 178.9 g were added to 800 mL of a DMF/THF(1/1) mixed solution. The solution was neutralized by adding 143 mL of N-methylmorpholine at 0° C. Next 147.5 mL of DCC was added to the solution and then it was stirred at 0° C. for 5 minutes and at room temperature for 15 hours. The reaction solution was concentrated under reduced pressure then 1000 mL of water was added to the residue obtained. After the product was washed twice with 500 mL of ethyl acetate, the aqueous layer was extracted three times with 1000 mL of n-butanol. The obtained n-butanol layer was concentrated under reduced pressure to obtain Z-Leu-Arg-OEt.
Workup
- concentrationThe reaction solution was concentrated under reduced pressure
- addition1000 mL of water was added to the residue
- customobtained
- washAfter the product was washed twice with 500 mL of ethyl acetate
- extractionthe aqueous layer was extracted three times with 1000 mL of n-butanol
- concentrationThe obtained n-butanol layer was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-240d48b4b2544434a2ee3797467bfba5
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06448031B1
Reaction notes
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