Water → HCID 86619842, compound

HRID 1994309Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][CH:8]2[CH2:12][O:11][S:10](=[O:13])[N:9]2[CH:14]([CH:22]([CH3:24])[CH3:23])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:5][CH:4]=1.O.C([O-])(O)=[O:29].[Na+].C(Cl)Cl>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]2[CH2:12][O:11][S:10](=[O:29])(=[O:13])[N:9]2[CH:14]([CH:22]([CH3:23])[CH3:24])[C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

t-Butyl 2-(4-(4-methoxybenzyl)-2-oxo-(1,2,3) oxathiazolidin-3-yl)-3-methylbutyrate (2.2 g; 5.7 mmol) was dissolved in acetonitrile (15 ml) and the reaction solution was cooled to 0° C. Then NaIO4 (1.47 g; 6.8 mmol), RuCl3.H2O (128.5 mg; 0.57 mmol) and water (15 ml) were added. The reaction solution was stirred at 0° C. for 5 minutes and then at RT for 30 minutes. This was followed by addition of NaHCO3 solution, extraction with CH2Cl2 (3×) and drying of the organic phase over NaSO4 and concentration in a rotary evaporator. The crude product was filtered through an SiO2 cartridge (10 g). t-Butyl 2-(4-(4-methoxybenzyl)-2,2-dioxo-(1,2,3)oxathiazolidin-3-yl)-3-methylbutyrate (2.02 g; 5.0 mmol) was obtained as a yellow oil. MS: 417.45 (M+NH4+); Rt: 1.86 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.)

Workup

waitat RT for 30 minutes
dry with materialdrying of the organic phase over NaSO4 and concentration in a rotary evaporator
filtrationThe crude product was filtered through an SiO2 cartridge (10 g)

Sources & evidence

ORD record: ord-388ad227bb4a47a79c98f5768c20ee58
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652143B2

Reaction notes

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