Water → HCID 10915235, compound

HRID 2301680Notes

Reaction equation

[C:1]([O:4][C@@H:5]1[CH2:9][C@@H:8]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:7][C@H:6]1[N:15]1[C:24]2[N:23]=[CH:22][N:21]=[C:19](O)[C:18]=2[N:17]=[CH:16]1)(=[O:3])[CH3:2].CN(C)C=O.S(Cl)([Cl:32])=O.O>C(Cl)Cl>[Cl:32][C:19]1[N:21]=[CH:22][N:23]=[C:24]2[C:18]=1[N:17]=[CH:16][N:15]2[C@@H:6]1[O:7][C@H:8]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH2:9][C@H:5]1[O:4][C:1](=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

32.7 g (97.2 mmols) of 2′,5′-di-O-acetyl-3′-deoxyinosine was suspended in 449 ml of methylene chloride in a 1-liter reactor, to which were added 30.1 ml (389 mmols) of dimethylformamide and 28.0 ml (389 mmols) of thionyl chloride, and reacted for about 7 hours while heating under reflux. The reaction mixture was cooled to 0° C., and then dropwise added to 500 ml of water that had been cooled at 0° C. to stop the reaction. The reaction mixture was separated into layers, and the organic layer was taken out, and washed with water, an aqueous saturated solution of sodium hydrogencarbonate and a saturated saline solution in that order. The solvent was evaporated, and 31.0 g of an oily product was obtained. This crude product was directly subjected to the next reaction.

Workup

customreacted for about 7 hours
temperaturewhile heating
temperatureunder reflux
temperaturehad been cooled at 0° C.
customthe reaction
customThe reaction mixture was separated into layers
washwashed with water
customThe solvent was evaporated

Sources & evidence

ORD record: ord-37833eba26b1447eb1a44e4641e13976
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500946B1

Reaction notes

Loading…