Hydrochloric Acid → 2',3'-di-O-methoxycarbonyl-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl) cytidine

HRID 420837Notes

Reaction equation

[CH3:1][O:2][C:3]([O:5][C@@H:6]1[C@H:10]([O:11][C:12]([O:14][CH3:15])=[O:13])[C@@H:9]([CH3:16])[O:8][C@H:7]1[N:17]1[CH:24]=[C:23]([F:25])[C:21]([NH2:22])=[N:20][C:18]1=[O:19])=[O:4].N1C=CC=CC=1.Cl[C:33]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:34].Cl>ClCCl>[CH3:1][O:2][C:3]([O:5][C@@H:6]1[C@H:10]([O:11][C:12]([O:14][CH3:15])=[O:13])[C@@H:9]([CH3:16])[O:8][C@H:7]1[N:17]1[CH:24]=[C:23]([F:25])[C:21]([NH:22][C:33]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:34])=[N:20][C:18]1=[O:19])=[O:4]

Participants

Conditions

Temperature: -2.5 °C

Procedure

35.8 g (0.099 mole) of the compound obtained in Example 2 was mixed with 163 ml of dichloromethane and 11 ml (0.136 mole) of pyridine, and stirred. After cooling the resulting mixture to −5 to 0° C., 15.7 ml (0.109 mole) of n-pentyl chloroformate was added dropwise thereto while maintaining the temperature of the reaction mixture at less than 0° C., followed adding the resulting mixture was warmed to room temperature and stirred for 2 hrs, 1 N HCl thereto. The organic layer was separated, successively washed with 163 ml of saturated sodium bicarbonate and 163 ml of water, dried over anhydrous sodium sulfate, and concentrated under a reduced pressure, to obtain 42.9 g of the title compound.

Workup

temperaturewhile maintaining the temperature of the reaction mixture at less than 0° C.
additionfollowed adding the resulting mixture
temperaturewas warmed to room temperature
stirringstirred for 2 hrs
customThe organic layer was separated
washsuccessively washed with 163 ml of saturated sodium bicarbonate and 163 ml of water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record: ord-1cbe1ce39d054b469a44e82153c6c608
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097706B2

Reaction notes

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