Oxalyl chloride → HCID 86585303, compound

Oxalyl chloride (4 ml, 46 mmol) was added to a solution of (3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (Justus Liebigs Ann. Chem., 1974, 11, 1856) (5 g, 23 mmol) in dichloromethane (100 ml). The solution was stirred at room temperature for two hours and then the solvent was evaporated under reduced pressure to yield a white solid. This was dissolved in ethyl acetate (80 ml) and N′-hydroxypropanimidamide (2.63 g, 30 mmol) was added followed by N-ethyldiisopropylamine (8.12 ml, 46 mmol). The reaction mixture was stirred at room temperature for 48 hours and then washed with saturated sodium hydrogencarbonate solution (50 ml) and brine (50 ml). The organic layer was separated, dried (anhydrous magnesium sulphate) and evaporated under reduced pressure to give the product as a dark yellow oil (5.85 g).

1. customthe solvent was evaporated under reduced pressure
2. customto yield a white solid
3. stirringThe reaction mixture was stirred at room temperature for 48 hours
4. washwashed with saturated sodium hydrogencarbonate solution (50 ml) and brine (50 ml)
5. customThe organic layer was separated
6. dry with materialdried (anhydrous magnesium sulphate)
7. customevaporated under reduced pressure

ORD record

ord-e098c59da3e64362a248b7f904bf4b62

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06624158B2