Sodium hydride → HCID 18962092, compound

HRID 1587537Notes

Reaction equation

HRID 1587537 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[H][H].[C:34]([O:38][C:39]([N:41]([CH2:52][CH2:53][CH2:54][CH2:55]Cl)[S:42]([C:45]1[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=1)(=[O:44])=[O:43])=[O:40])([CH3:37])([CH3:36])[CH3:35]>CN(C)C=O>[C:34]([O:38][C:39]([N:41]([S:42]([C:45]1[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=1)(=[O:44])=[O:43])[CH2:52][CH2:53][CH2:54][CH2:55][N:13]([S:10]([C:7]1[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=1)(=[O:11])=[O:12])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([S:22]([C:25]1[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=1)(=[O:23])=[O:24])[CH2:55][CH2:54][CH2:53][CH2:52][N:41]([C:39]([O:38][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:40])[S:42]([C:45]1[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=1)(=[O:44])=[O:43])=[O:40])([CH3:37])([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 4135031HCID 4135031, compoundHCID 18962091HCID 18962091, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18962092HCID 18962092, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

Suspend sodium hydride (4.8 g, 0.2 mol) in anhydrous dimethylformamide (100 mL), cool to 0° C. and place under a nitrogen atmosphere. Add, by dropwise addition, a solution 1,9-bis[(4-methylphenyl)sulfonyl]-1,9-diazanonane (43.8 g, 0.1 mol) in dimethylformamide. Stir until evolution of hydrogen ceases. Add, by dropwise addition, a solution of N-(t-butyloxycarbonyl)-N-[(4-methylphenyl)sulfonyl]-4-chlorobutylamine (72.4 g, 0.2 mol) in dimethylformamide (100 mL). Stir overnight at room temperature then carefully quench with saturated ammonium chloride. Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatogaphy to give the title compound.

Workup

  1. additionAdd, by dropwise addition
  2. additionAdd, by dropwise addition
  3. customthen carefully quench with saturated ammonium chloride
  4. extractionExtract into ethyl acetate
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo
  7. customPurify by silica gel chromatogaphy

Sources & evidence

ORD record
ord-a2f5db56e3b244039e13677b4515dc22
Source dataset
uspto-grants-1993_06
Patent number
US05217964

Reaction notes

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