Piperidine → 3-amino-N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-L-alanine, methyl ester
Reaction equation
[Cl:1][C:2]1[CH:34]=[C:33]([C:35]([NH:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([OH:45])[CH:40]=2)=[O:36])[CH:32]=[CH:31][C:3]=1[C:4]([NH:6][C@H:7]([C:27]([O:29][CH3:30])=[O:28])[CH2:8][NH:9]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)=[O:5].N1CCCCC1>ClCCl.CO>[NH2:9][CH2:8][C@@H:7]([C:27]([O:29][CH3:30])=[O:28])[NH:6][C:4](=[O:5])[C:3]1[CH:31]=[CH:32][C:33]([C:35]([NH:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([OH:45])[CH:40]=2)=[O:36])=[CH:34][C:2]=1[Cl:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester (1.17 g, 1.9 mmol) in dichloromethane/methanol (2:1) was added to piperidine (1.1 mL, 11.2 mmol). The reaction mixture was stirred for 4 h at room temperature and then more piperidine (1.1 mL, 11.2 mmol) was added. The solution was stirred at room temperature overnight, then it was concentrated and the residue was chromatographed (0-40% methanol/dichloromethane) to give 3-amino-N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-L-alanine, methyl ester (760 mg, 100%) as a pale yellow solid.
Workup
- stirringThe solution was stirred at room temperature overnight
- concentrationit was concentrated
- customthe residue was chromatographed (0-40% methanol/dichloromethane)
Sources & evidence
- ORD record
- ord-34d02f7e8a744f158f72b9f47fb36638
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06803384B2
Reaction notes
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