Methyl iodide → (2S,3R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxybutanoic acid

In a THF solution containing 0.8 g of Boc-Thr-OH, 100 mg of sodium hydride (60% in oil) was added under ice cooling and the resultant mixture was stirred for 30 min at room temperature. Further, 2.8 ml of methyl iodide was added and the obtained reaction mixture was stirred overnight at room temperature. The reaction mixture was evaporated under reduced pressure and the resultant residue was redissolved in ethyl acetate, washed with 5% sodium hydrogensulfite aqueous solution, water and saturated sodium chloride aqueous solution, successively, and dried over anhydrous sodium sulfate. The dried solution was evaporated under reduced pressure, dissolved in methanol, mixed with DCHA and reevaporated. Ether-hexane was added to the residue to give 0.55 g of the title compound as its DCHA salt.

1. additionwas added under ice cooling
2. customthe obtained reaction mixture
3. customThe reaction mixture was evaporated under reduced pressure
4. dissolutionthe resultant residue was redissolved in ethyl acetate
5. washwashed with 5% sodium hydrogensulfite aqueous solution, water and saturated sodium chloride aqueous solution
6. dry with materialsuccessively, and dried over anhydrous sodium sulfate
7. customThe dried solution was evaporated under reduced pressure
8. dissolutiondissolved in methanol
9. additionmixed with DCHA
10. customreevaporated
11. additionEther-hexane was added to the residue

ORD record

ord-993ac4fef23748b9b84fc2b29d088d4b

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313094B1