Methanesulfonyl chloride → HCID 86759942, compound

HRID 1743730Notes

Reaction equation

HRID 1743730 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][CH2:9][CH:10]([OH:20])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:5][CH:4]=1)#[N:2].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:23][S:24]([O:20][CH:10]([CH2:11][NH:12][C:13]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:19])[CH2:9][CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:22][CH:21]=1)(=[O:26])=[O:25]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22235406HCID 22235406, compound

Product 1

HCID 86759942HCID 86759942, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Conditions

Temperature
0 °C

Procedure

tert-Butyl 4-(4-cyanophenoxy)-2-hydroxybutylcarbamate (38.1 g, 120 mmol; from step (f) above) and 4-(dimethylamino)pyridine (10 mol %) was dissolved in pyridine (200 mL). The mixture was cooled to 0° C. Methanesulfonyl chloride (10.7 mL, 0.136 mol) was added dropwise at 0° C. The mixture was allowed to reach r.t before the pyridine was evaporated. DCM was added, the solution was washed with 2 M HCl and water, dried and then evaporated. The compound was purified by chromatography on silica, eluting with DCM:ethyl acetate (95:5) to give 27 g of the sub-title compound.

Workup

  1. customwas evaporated
  2. additionDCM was added
  3. washthe solution was washed with 2 M HCl and water
  4. customdried
  5. customevaporated
  6. customThe compound was purified by chromatography on silica
  7. washeluting with DCM:ethyl acetate (95:5)

Sources & evidence

ORD record
ord-41b21fb0ff594e17bcdffc2ee3bacdca
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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