* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sodium hydroxide; citric acid; In water; tert-butyl alcohol;
E) Preparation of N,N'-di-Boc-S-methylisothiourea To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL). After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL). The organic phase was washed once with water (250 mL), three times with 1 N citric acid (250 mL) and once again with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.
42 g (62%)
With sodium hydroxide; citric acid; In water; tert-butyl alcohol;
E) Preparation of N,N'-di-Boc-S-methylisothiourea. To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL). After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL). The organic phase was washed once with water (250 mL), three times with 1N citric acid (250 mL) and once again with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.
42 g (62%)
With sodium hydroxide; citric acid; In water; tert-butyl alcohol;
E) Preparation of N,N'-di-Boc-S-methylisothiourea To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL). After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL). The organic phase was washed once with water (250 mL), three times with 1N citric acid (250 mL) and once again with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.
42 g (62%)
With sodium hydroxide; citric acid; In water; tert-butyl alcohol;
E) Preparation of N,N'-di-Boc-S-methylisothiourea To a stirring solution of di-t-butyl dicarbonate (100 g, 458 mmol) in t-butanol (300 mL) was added a solution of bis-S-methylisothiourea sulfate (32.7 g, 117 mmol) in water (150 mL), followed by a solution of sodium hydroxide (19.2 g, 480 mmol) in water (150 mL). After stirring for 48 hours, the mixture was concentrated to approximately one-third of the original volume in vacuo and diluted with diethyl ether (500 mL). The organic phase was washed once with water (250 mL), three times with 1N citric acid (250 mL) and once again with water (250 mL). The organic phase was then dried (MgSO4), filtered and concentrated in vacuo to give 42 g (62percent) of a white solid.
Step B Tert-butyl (2E)-3-amino-2-aza-3-[(tert-butoxy)carbonylamino]prop-2-enoate Tert-butyl (2Z)-2-aza-3-[(tert-butoxy)carbonylamino]-3-methylthioprop-2-enoate was dissolved in MeOH (0.1M) followed by addition of 1N NH4OH (5 eq). After stirring overnight the solution was concentrated in vacuo to afford a colorless solid. EI-MS m/z 411 (M+H)+.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
