Methanesulfonyl chloride → HCID 13923448, compound

HRID 232358Notes

Reaction equation

HRID 232358 reaction equation
[CH2:1]([C:3]1[C:4](=[O:37])[NH:5][C:6](=[O:36])[N:7]([CH:35]=1)[C@@H:8]1[O:34][C@H:12]([CH2:13][O:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@H:10]([OH:11])[CH2:9]1)[CH3:2].[CH3:38][S:39](Cl)(=[O:41])=[O:40]>N1C=CC=CC=1>[CH2:1]([C:3]1[C:4](=[O:37])[NH:5][C:6](=[O:36])[N:7]([CH:35]=1)[C@@H:8]1[O:34][C@H:12]([CH2:13][O:14][C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@@H:10]([O:11][S:39]([CH3:38])(=[O:41])=[O:40])[CH2:9]1)[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 13062021HCID 13062021, compound

Product 1

HCID 13923448HCID 13923448, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 16.0 g of 2'-deoxy-5-ethyl-5'-O-trityluridine and 6.8 ml of methanesulfonyl chloride in 140 ml of pyridine was stored at 0° C. overnight. 3 g of ice were added, the mixture was stored at 0° C. for 1 hour and then poured into 1500 ml ice/water. The resulting solid was collected by filtration, washed with 500 ml of water and dried to yield 17.35 g of 2'-deoxy-5-ethyl-3'-O-methanesulfonyl-5'-O-trityluridine in the form of a white solid which was used in the next step without further purification.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with 500 ml of water
  3. customdried

Sources & evidence

ORD record
ord-db1eeaaada5d4373977bf823adc8ee24
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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