2-Mesitylenesulfonyl chloride → 3-tert-Butoxycarbonylamino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH2:14])[CH2:5][NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[C:16]1([CH3:28])[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[S:24](Cl)(=[O:26])=[O:25].CCN(C(C)C)C(C)C>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:14][S:24]([C:17]1[C:18]([CH3:23])=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=1[CH3:28])(=[O:26])=[O:25])[CH2:5][NH:6][C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 3-tert-Butoxycarbonylamino-2-aminopropionic acid methyl ester (3.5 g, 13.7 mmol), mesitylsulfonyl chloride (3.9 g, 17.8 mmol), DIEA (7.2 mL, 41.1 mmol) in dichloromethane (100 mL) was stirred at 0° C. for one hour and overnight at room temperature. The solvent was removed and the crude reaction product was taken up in ethyl acetate (340 mL). The solution was washed with 5% solution of sodium carbonate (30 mL), 5% solution of hydrochloric acid (30 mL), with saturated sodium chloride solution (30 mL). Solvent was than dried over sodium sulfate and evaporated. Purification of the residue on silica gel (10%MeOH-EtOAc) gave 5.00 g of pure compound O-1 (84% yield).
Workup
- customThe solvent was removed
- customthe crude reaction product
- washThe solution was washed with 5% solution of sodium carbonate (30 mL), 5% solution of hydrochloric acid (30 mL), with saturated sodium chloride solution (30 mL)
- dry with materialthan dried over sodium sulfate
- customevaporated
- customPurification of the residue on silica gel (10%MeOH-EtOAc)
Sources & evidence
- ORD record
- ord-1e9bfc59ac1f4141a3284f99a1723b56
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06274620B1
Reaction notes
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