Methanesulfonyl chloride → HCID 13923448, compound

HRID 2119032Notes

Reaction equation

HRID 2119032 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, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-ethyl-5'-O-trityl-2'-deoxyuridine (7.5 g, 15 mmole) in dry pyridine (50 ml), methanesulfonyl chloride (4.0 g, 35 mmole) is added while cooling in an ice-water bath. The mixture is stirred for one hour at around 0° C. and followed by allowing the temperature to rise to room temperature. At this point, tlc indicates no remaining starting materials. The mixture is then poured into an ice-water mixture (1.5 liters) while stirring, the water is decanted, and the product is washed with cold water several times, dissolved in chloroform and dried (over MgSO4). Finally, the solvent is evacuated in vacuo to obtain a syrup (7.6 g, 90%). This material is sufficiently pure to carry out the next reaction without further purification. However, an analytical sample can be obtained by column chromatography or tlc using chloroform as an eluent.

Workup

  1. temperaturewhile cooling in an ice-water bath
  2. customto rise to room temperature
  3. stirringwhile stirring
  4. customthe water is decanted
  5. washthe product is washed with cold water several times
  6. dissolutiondissolved in chloroform
  7. dry with materialdried (over MgSO4)
  8. customFinally, the solvent is evacuated in vacuo

Sources & evidence

ORD record
ord-e4b55f4572754aa4adcf25de51be0a5b
Source dataset
uspto-grants-1987_07
Patent number
US04681933

Reaction notes

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