3-(5-(Benzyloxy)-2-pyridinyl)-N-(tert-butoxycarbonyl)alanine → Methyl 4-((3-(5-(benzyloxy)pyridin-2-yl)-2-(tert-butoxycarbonylamino)propanamido)methyl)benzoate
Reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][CH:28]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:29](O)=[O:30])=[N:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][CH:28]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:29]([NH:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=2)=[O:30])=[N:25][CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of methyl 4-(aminomethyl)benzoate (2 g, 10 mmol), 3-(5-(benzyloxy)-pyridine-2-yl)-2-(tert-butoxycarbonylamino) propanoic acid (1.04 g, 11 mmol), and 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (2 g, 10.4 mmol) in 50 mL dichloromethane was stirred at room temperature for 2 h (monitored by TLC). The mixture was extracted with water and dried over magnesium sulfate. The residue was purified by chromatography (EA:Hex=1:1) to give the title compound (1.5 g, 49%). NMR (400 MHz in CDCl3, Bruker AVANCE-400): δ 1.31 (s, 9H, Boc), 2.90 (m, 2H, CH2), 3.81 (s, 3H, OMe) 4.30 (m, 2H, CH2), 4.33 (m, 1H, CH), 5.12 (s, 2H, OBn), 6.97-7.09 (d, 1H, J=3.5 Hz, Ar—H), 7.15 (d, 1H, J=8.53 Hz, Ar—H), 7.24˜7.46 (m, 8H, Ar—H), 7.84, (d, 2H, Ar—H, J=8.24 Hz), 8.24 (br, 1H, NH), 8.43 (br, 1H, NH).
Workup
- extractionThe mixture was extracted with water
- dry with materialdried over magnesium sulfate
- customThe residue was purified by chromatography (EA:Hex=1:1)
Sources & evidence
- ORD record
- ord-97f9d09a06444cbea2e53dfc6ae1971a
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242282B2
Reaction notes
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