Hydroxylamine → HCID 86585705, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C@@H:5]([CH2:18][CH2:19][CH2:20][CH3:21])[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](C(O)=O)=[O:14])=[O:7].CC[N:25](C(C)C)C(C)C.CN(C([O:39][N:40]1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:56]O.C([O-])(=O)CCC([O-])=O>CN(C=O)C>[OH:39][NH:40][C:3](=[O:2])[CH2:4][C@@H:5]([CH2:18][CH2:19][CH2:20][CH3:21])[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([NH2:56])=[O:14])=[O:7].[CH3:1][O:2][C:3](=[O:22])[CH2:4][C@@H:5]([CH2:18][CH2:19][CH2:20][CH3:21])[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([NH2:25])=[O:14])=[O:7]Participants
8
Reactant 5
Product 2
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To methyl-3-(R)-butyl-3-(2-(S)-carboxycarbonylpyrrolidin-1-ylcarbonyl)-propionate E-2 (100 mg) in DMF (1 mL) was added an amine (1 equivalent), DIEA (2.5 equivalents) and HATU (1 equivalent) and the reaction stirred for 4 h. The solution was then cooled to 0° C., 50% aqueous hydroxylamine was added (400 μL), and the reaction stirred at 4° C. for 4 hours to 3 days, depending upon the succinate. The crude reaction mixture was then purified by preparative reverse-phase (C18) HPLC to afford the desired compound methyl-3-(R)-butyl-3-(2-(S)-aminocarbonylpyrrolidin-1-ylcarbonyl)propionate E-3.
Workup
- stirringthe reaction stirred at 4° C. for 4 hours to 3 days
- customThe crude reaction mixture
- customwas then purified by preparative reverse-phase (C18) HPLC
Sources & evidence
- ORD record
- ord-aad064ee5e9e4ee7aca40a04c7d40a3a
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06797820B2
Reaction notes
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