Pyridine → (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl fluoride
Reaction equation
[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:14](O)=[O:15])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:2].C(OC(NC[C@@H](CCCCC)C(O)=O)=O)C1C=CC=CC=1.N1C=CC=CC=1.[F:49]C1N=C(F)N=C(F)N=1>ClCCl>[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:14]([F:49])=[O:15])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 250 mL round-bottomed flask was added (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoic acid (WO 2003101442, also named (2R)-[(benzyloxyformylamino)methyl]heptanoic acid) (4.40 g, 15 mmol) in dichloromethane (60 mL), followed by pyridine (1.453 mL, 18.00 mmol) and 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) (2.168 g, 16.05 mmol). The reaction mixture was stirred at room temperature for 2 h, then was diluted with DCM, and washed with 5% Citric acid (150 mL) and sat. NaHCO3 (150 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography to provide (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl fluoride as a colorless oil (1.88 g, 42%). LCMS: (M+H)+: 296.0.
Workup
- washwashed with 5% Citric acid (150 mL) and sat. NaHCO3 (150 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-5a54afd195dd4ab9ad35a00adf7aaa16
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901119B2
Reaction notes
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