Sodium hydride → HCID 86754520, compound

HRID 618825Notes

Reaction equation

HRID 618825 reaction equation
ClC1C=C2C(=CC=1)OC(C)(C)C(O)C2CS(N[CH2:20][C:21]([O:23][CH3:24])=[O:22])(=O)=O.[Cl:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[O:32][C:31]([CH3:37])([CH3:36])[CH:30]([OH:38])[CH:29]2[NH:39][S:40]([CH3:43])(=[O:42])=[O:41].[H-].[Na+].BrCC(OC)=O>CN(C=O)C.CC(=O)OCC>[Cl:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[O:32][C:31]([CH3:37])([CH3:36])[CH:30]([OH:38])[CH:29]2[N:39]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[S:40]([CH3:43])(=[O:42])=[O:41]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 21848667HCID 21848667, compoundHCID 86754521HCID 86754521, compound

Product 1

HCID 86754520HCID 86754520, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl [(6-chloro-3-hydroxy-2,2-dimethylchroman-4-yl)methanesulfonylamino]acetate A solution of 3.0 g (10 mmol) of N-(6-chloro-3-hydroxy-2,2-dimethylchroman-4-yl)methanesulfonamide was added dropwise to a solution of 0.33 g (11.3 mmol) of 80 percent sodium hydride in 25 ml of DMF and the mixture was additionally stirred at RT for 1 h. 1.53 g (10 mmol) of methyl bromoacetate were then added, the mixture was stirred overnight at RT and then the solvent was stripped off in vacuo. The residue was taken up in EA and water, the organic phase was concentrated and the product was purified by chromatography on silica gel using cyclohexane/ethyl acetate 9:1. 2.0 g of methyl [(6-chloro-3-hydroxy-2,2-dimethylchroman-4-yl)-methanesulfonylamino]acetate were obtained; m.p. 148-150° C.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. concentrationwater, the organic phase was concentrated
  3. customthe product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-eee2901514d14067b387aef79e37b736
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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