Trichloroisocyanuric Acid → (3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylic acid

Temperature

0 °C

To a solution of (3aS,5S,6R,6aS)-5-(Hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-ol (14.6 g, 76.7 mmol), NaHCO3 (19.3 g, 230.3 mmol) and NaBr (1.6 g, 15.4 mmol) in acetone/water (120/40 mL) was added TEMPO (2,2,6,6-Tetramethyl-1-piperidinyloxy free radical) (0.24 g, 1.5 mmol) at room temperature. The mixture was cooled to 0° C., and trichloroisocyanuric acid (17.8 g, 76.7 mmol) was then added in portions. The suspension was stirred for 12 h at room temperature. Methanol (2.0 mL) was added and the mixture was stirred for 2 h at room temperature. The mixture was filtered, washed with acetone (twice, 20 mL per wash). The organic solvent was removed under vacuum and the aqueous layer was extracted with EtOAc and the organic layer was concentrated in vacuo. Acetone was added and the mixture was filtered. The filtrate was concentrated to afford the desired acid (9.0 g, 58%) as a pale yellow solid.

1. stirringthe mixture was stirred for 2 h at room temperature
2. filtrationThe mixture was filtered
3. washwashed with acetone (twice, 20 mL
4. washper wash)
5. customThe organic solvent was removed under vacuum
6. extractionthe aqueous layer was extracted with EtOAc
7. concentrationthe organic layer was concentrated in vacuo
8. additionAcetone was added
9. filtrationthe mixture was filtered
10. concentrationThe filtrate was concentrated

ORD record

ord-896a85b960874ac3b7a13446da8c3503

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371303B2