Dichloromethane → chloromethyl (2S)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[CH2:21](Cl)[Cl:22]>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.O>[Cl:22][CH2:21][O:11][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:13]([CH3:15])[CH3:14]Participants
6
Procedure
To a mixture of (S)-2-(t-butoxycarbonylamino)-3-methylbutanoic acid (28.6 g, 130 mmol) and NaHCO3 (44 g, 520 mmol) and Bu4NHSO4 (4.4 g, 13 mmol) in DCM (200 mL) and water (200 mL) was added chloromethyl sulfochloridate (26 g, 158 mmol) at 0° C. The mixture was stirred at room temperature for 24 hours, and then was extracted with DCM (3×150 mL). The combined organic layers were washed with water (2×300 mL), and the DCM layer was purified by flash column (petroleum ether:EA=15:1) to yield the title compound as a yellow solid (35 g). LC-MS: 266 [M+H]+.
Workup
- additionwas added chloromethyl sulfochloridate (26 g, 158 mmol) at 0° C
- extractionwas extracted with DCM (3×150 mL)
- washThe combined organic layers were washed with water (2×300 mL)
- customthe DCM layer was purified by flash column (petroleum ether:EA=15:1)
Sources & evidence
- ORD record
- ord-63773046c64843d28ce9230623933470
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108934B2
Reaction notes
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