Methanesulfonyl chloride → HCID 123738137, compound

HRID 1289888Notes

Reaction equation

HRID 1289888 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:60]=[CH:59][C:11]([C:12]([O:27][CH2:28][C@@:29]2([CH:51]=[CH:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][OH:58])[O:33][C@@H:32]([N:34]3[CH:42]=[C:40]([CH3:41])[C:38](=[O:39])[NH:37][C:35]3=[O:36])[CH2:31][C@@H:30]2[O:43][SiH2:44][C:45]([CH3:50])([CH3:49])[CH:46]([CH3:48])[CH3:47])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1>N1C=CC=CC=1>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([O:27][CH2:28][C@@:29]2([CH:51]=[CH:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][O:58][S:2]([CH3:1])(=[O:4])=[O:3])[O:33][C@@H:32]([N:34]3[CH:42]=[C:40]([CH3:41])[C:38](=[O:39])[NH:37][C:35]3=[O:36])[CH2:31][C@@H:30]2[O:43][SiH2:44][C:45]([CH3:49])([CH3:50])[CH:46]([CH3:47])[CH3:48])([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:11]2[CH:59]=[CH:60][C:8]([O:7][CH3:6])=[CH:9][CH:10]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 123138873HCID 123138873, compound

Product 1

HCID 123738137HCID 123738137, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (96 μL, 1.22 mmole) was added dropwise to Compound (4) (250 mg, 0.32 mmole) in dry pyridine (3 mL) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 2 hours and the reaction was quenched by the dropwise addition of methanol (1.5 mL). The yellow solution was poured into water (20 mL) and the layers were separated. The organic phase was washed with brine (20 mL), dried over magnesium sulfate and concentrated to a white solid (0.41 g) under reduced pressure. (Routinely, this crude material was used directly in the next step). The crude product (0.41 g) was purified by column chromatography on silica gel using ethyl acetate/hexane mixtures for elution. 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(dimethyl-1,1-dimethylethyl) silyl]-4'-(7-methanesulfonyloxy-1-hepten-1-yl)-thymidine (241 mg, 87.5%) was obtained as a white solid. Recrystallization from hexane/dichloromethane gave a sample with m.p. 72°-75° C.

Workup

  1. customthe reaction was quenched by the dropwise addition of methanol (1.5 mL)
  2. additionThe yellow solution was poured into water (20 mL)
  3. customthe layers were separated
  4. washThe organic phase was washed with brine (20 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to a white solid (0.41 g) under reduced pressure
  7. customThe crude product (0.41 g) was purified by column chromatography on silica gel
  8. washmixtures for elution

Sources & evidence

ORD record
ord-aac545ed1c8e48da956d5a845fd41501
Source dataset
uspto-grants-1998_05
Patent number
US05750343

Reaction notes

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