Sodium Hydroxide → tert-Butyl 3-thioureidopropylcarbamate
Reaction equation
C([NH:9][C:10](=[S:23])[NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=O)C1C=CC=CC=1.[OH-].[Na+]>CO>[NH:11]([CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[C:10]([NH2:9])=[S:23]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of material from Example 58 (6.89 g, 20.43 mmol) in MeOH (40 mL) is slowly added aqueous 5M NaOH (4.49 mL, 22.47 mmol) and the reaction is allowed to stir for 1 h at room temp. The solvent is removed in vacuo, the residue is neutralized with acetic acid and partitioned between water and EtOAc. The water layer is extracted with EtOAC, the organic layers are combined, washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give 3.43 g (50.2%) of the title compound. LC/MS (Condition A): ret. T=2.54 min, (M+Na) 256.13.