Sodium Hydroxide → 4-(3-{[(Tert-butoxy)carbonyl]amino}prop-1-yn-1-yl)benzoic acid

反応式

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]#[C:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]#[C:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

実験手順

Methyl 4-(3-t-butoxycarbonylaminoprop-1-ynyl)benzoate (1.09 g, 38 mmol, reference example 81) is dissolved in MeOH (15 mL) and to this solution added NaOH (0.15 g, 38 mmol) dissolved in water (5 mL). This mixture is heated to reflux. After 5 hours, the solvent is removed in vacuo and CH2Cl2 and 1N HCl added to the residue. The organic layer is washed with 1N HCl, water and brine, then dried over magnesium sulfate. The solvent is removed in vacuo to give a white solid (0.60 g, 57% yield): 1H NMR (300 MHz, CD3OD) d 7.86 (d, 2H), 7.39 (d, 2H), 3.98 (s, 2H), 1.38 (s, 9H).