Methanesulfonyl chloride → HCID 18635820, compound

HRID 1638980Notes

Reaction equation

HRID 1638980 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][CH:12]([OH:20])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:8][C@@H:7]([N:21]2[CH:28]=[C:27]([CH2:29][CH3:30])[C:25](=[O:26])[NH:24][C:22]2=[O:23])[CH2:6]1)(=[O:3])[CH3:2].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][CH:12]([O:20][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:8][C@@H:7]([N:21]2[CH:28]=[C:27]([CH2:29][CH3:30])[C:25](=[O:26])[NH:24][C:22]2=[O:23])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 18635823HCID 18635823, compound

Product 1

HCID 18635820HCID 18635820, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 300 mg of 3'-O-acetyl-5'-[2(RS)-hydroxy-3-phenylpropyl]-2',5'-dideoxy-5-ethyluridine and 0.2 ml of methanesulphonyl chloride in 5 ml of pyridine was left to stand at 0° C. overnight. The mixture was poured on to 40 ml of ice/water, stirred and extracted with 40 ml of ethyl acetate. The extract was dried over anhydrous sodium sulphate and evaporated to yield 330 mg of 3'-O-acetyl-2',5'-dideoxy-5-ethyl-5'-[2(RS)-methanesulphonyloxy-3-phenylpropyl]uridine.

Workup

  1. extractionextracted with 40 ml of ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-f111956df0794ff1872f12cf93dbf80d
Source dataset
uspto-grants-1989_11
Patent number
US04882316

Reaction notes

Loading…