Sodium hydride → HCID 22827700, compound

HRID 2418302Notes

Reaction equation

HRID 2418302 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH3:17])[N:5]([C:13](=[O:16])[CH2:14][OH:15])[C:6]1[C:10]([CH3:11])=[CH:9][S:8][C:7]=1[CH3:12].[H-].[Na+].[CH3:21][N:22]([CH3:27])[S:23](Cl)(=[O:25])=[O:24]>C(COC)OC>[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH3:17])[N:5]([C:13](=[O:16])[CH2:14][O:15][S:23]([N:22]([CH3:27])[CH3:21])(=[O:25])=[O:24])[C:6]1[C:10]([CH3:11])=[CH:9][S:8][C:7]=1[CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 22827701HCID 22827701, compound

Product 1

HCID 22827700HCID 22827700, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

8.13 g (0.03 mol) N-(hydroxyacetyl)-N-(2,4-dimethylthien-3-yl)-alanine-methylester is added in portions to a slurry of 1.05 g (0.035 mol) sodium hydride (80% in mineral oil) in 50 ml dry dimethoxyethane with stirring at 10°-15° under a blanket of nitrogen. The mixture is stirred at room temperature for half an hour, and then are added 4.3 g (0.03 mol) dimethylsulphamic acid chloride. The mixture is stirred for 18 hours at 50°, then cooled to room temperature, filtered, concentrated in vacuo, the residue taken up in CHCl3, washed thoroughly with water, dried over MgSO4 and evaporated in vacuo to yield the title compound.

Workup

  1. stirringThe mixture is stirred at room temperature for half an hour
  2. stirringThe mixture is stirred for 18 hours at 50°
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washwashed thoroughly with water
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-cbf7c56423f94ea39946af72d25b49f6
Source dataset
uspto-grants-1984_09
Patent number
US04472425

Reaction notes

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