Diisopropylethylamine → HCID 178502742, compound
Reaction equation
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:20](O)=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[CH3:30]CN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.[N:46]1([O:55][P+](N(C)C)(N(C)C)N(C)C)[C:50]2C=CC=CC=2N=N1>CN(C=O)C>[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[C@H:2]([C:20]([N:46]([O:55][CH3:30])[CH3:50])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:10])=[O:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of Boc-Arg(Tos)—OH (2 g, 4.7 mmol) in DMF (20 mL) at 0° C. is added MeNHOMeHCl (1 g, 10.3 mmol), DIEA (6 mL) and BOP (2.5 g, 5.6 mmol). The solution is stirred at 0° C. for 10 hours. DMF is evaporated by vacuum. The oily residue is dissolved in EtOAc (200 mL) and water (20 mL). The organic layer is washed with sat. NaHCO3, water (20 mL), 1M HCl (10 mL) and sat. NaCl (2×20 mL). The organic layer is dried over MgSO4, filtered and evaporated to give a suspension. The suspension is filtered, washed with cold EtOAc (10 mL) and dried to give Boc-Arg(Tos)-N(Me)OMe, shown above, (1.5 g, 70% yield). FAB-MS (M+H)+=472
Workup
- customDMF is evaporated by vacuum
- dissolutionThe oily residue is dissolved in EtOAc (200 mL)
- washThe organic layer is washed with sat. NaHCO3, water (20 mL), 1M HCl (10 mL) and sat. NaCl (2×20 mL)
- dry with materialThe organic layer is dried over MgSO4
- filtrationfiltered
- customevaporated
- customto give a suspension
- filtrationThe suspension is filtered
- washwashed with cold EtOAc (10 mL)
- customdried
Sources & evidence
- ORD record
- ord-6f2c80abd82943bf8a21e42d31589760
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06525076B1
Reaction notes
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