4-Methylmorpholine → HCID 178479344, compound
Reaction equation
CC(OC([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][CH2:11][CH2:12][N:13]=[C:14]([NH:16][N+:17]([O-:19])=[O:18])[NH2:15])=O)(C)C.[Cl:23][C:24](OCC(C)C)=O.CN1CCOCC1.[ClH:38].C(O)C>O1CCCC1>[NH2:8][C@H:9]([C:20]([CH2:24][Cl:23])=[O:22])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:15])[NH:16][N+:17]([O-:19])=[O:18].[ClH:38]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
Boc Arg(NO2)OH (5.0 g, 15.6 mmol) was dissolved in 60 ml of tetrahydrofuran (THF) and was allowed to react with isobutyl chloroformate (2.06 ml, 15.6 mmol) in the presence of N-methylmorpholine (1.72 ml, 15.6 mmol) for 10 min at -20° C. The mixed anhydride preparation was filtered, and the filtrate was added to 120 ml of ethereal diazomethane. After stirring the reaction solution for 30 min at 0° C., 80 ml of ether was added. The product crystallized from the reaction solution in the cold. The Boc-Arg(HO2)CHNH2 product was dissolved in a minimum volume of THF and was allowed to react with ethanol HCl (20 mmol) at room temperature until nitrogen evolution ceased.
Workup
- filtrationwas filtered
- additionthe filtrate was added to 120 ml of ethereal diazomethane
- addition80 ml of ether was added
- customThe product crystallized from the reaction solution in the cold
- dissolutionThe Boc-Arg(HO2)CHNH2 product was dissolved in a minimum volume of THF
Sources & evidence
- ORD record
- ord-f5ac0f6aeb734f449c225bf22b32321d
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05023236
Reaction notes
Loading…