Water → HCID 86619840, compound

Temperature

-78 °C

t-Butyl 2-(2-hydroxy-1-(4-methoxyphenyl)ethylamino)-3-methylbutyrate (2.5 g; 7.73 mmol) was introduced into CH2Cl2 (200 ml), and the solution was cooled to −78° C. Addition of pyridine (3.12 ml; 38.65 mmol) was followed by slow dropwise addition of thionyl chloride (0.67 ml; 9.27 mmol). The reaction mixture was stirred for 1 h, during which the temperature was allowed to rise to 0° C. The reaction mixture was partitioned between aqueous 1% strength HCl/CH2Cl2 and extracted with CH2Cl2 (2×). The combined organic phases were washed with saturated NaHCO3 solution and dried over MgSO4, and the solvent was removed in a rotary evaporator. The residue was taken up in acetonitrile (20 ml) and cooled to 0° C. Then NaIO4 (1.82 g; 8.5 mmol), RuCl3.H2O (14.43 mg; 0.077 mmol) and water (20 ml) were added. The reaction mixture was stirred at 0° C. for 5 minutes and then at RT for a further 20 minutes. It was then partitioned between saturated NaHCO3 solution/CH2Cl2 and extracted with CH2Cl2 (2×). The combined organic phases were washed with saturated NaHCO3 and dried over MgSO4, and the solvent was removed in a rotary evaporator. Purification by chromatography resulted in t-butyl 2-(4-(4-methoxyphenyl)-2,2-dioxo-(1,2,3)oxathiazolidin-3-yl)-3-methylbutyrate (2.5 g; 6.48 mmol). MS: 403.15 (M+NH4+); Rt: 1.82 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.).

1. customto rise to 0° C
2. customThe reaction mixture was partitioned between aqueous 1% strength HCl/CH2Cl2
3. extractionextracted with CH2Cl2 (2×)
4. washThe combined organic phases were washed with saturated NaHCO3 solution
5. dry with materialdried over MgSO4
6. customthe solvent was removed in a rotary evaporator
7. temperaturecooled to 0° C
8. stirringThe reaction mixture was stirred at 0° C. for 5 minutes
9. waitat RT for a further 20 minutes
10. customIt was then partitioned between saturated NaHCO3 solution/CH2Cl2
11. extractionextracted with CH2Cl2 (2×)
12. washThe combined organic phases were washed with saturated NaHCO3
13. dry with materialdried over MgSO4
14. customthe solvent was removed in a rotary evaporator
15. customPurification by chromatography

ORD record

ord-4a1bb706416c4a35af7aac8fa8593fd6

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652143B2