Benzyl Bromide → HCID 19757890, compound

HRID 1587535Notes

Reaction equation

HRID 1587535 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][N:18]([C:50](=[O:57])[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([C:42](=[O:49])[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:27][CH2:28][CH2:29][CH2:30][NH:31][S:32]([C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[H][H].[CH2:60](Br)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>CN(C)C=O>[C:61]1([CH2:60][N:31]([S:32]([C:35]2[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=2)(=[O:34])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][N:26]([C:42](=[O:49])[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][N:18]([C:50](=[O:57])[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:17][CH2:16][CH2:15][CH2:14][N:13]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[S:10]([C:7]2[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=2)(=[O:11])=[O:12])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 19757919HCID 19757919, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19757890HCID 19757890, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

Suspend sodium hydride (48 mg, 2 mmol) in anhydrous dimethylformamide (2 mL), cool to 0° C. and place under a nitrogen atmosphere. Add, by dropwise addition, a solution 1,19-bis[(4-methylphenyl)sulfonyl]-6,14-bis(benzoyl)-1,6,14,19-tetraazanonadecane (78 mg, 1 mmol) in dimethylformamide (2 mL). Stir until evolution of hydrogen ceases. Add, by dropwise addition, a solution of benzylbromide (34 mg, 2 mmol) in dimethylformamide (2 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-1285dfdd94944ba1a38619a6183ba191
Source dataset
uspto-grants-1993_06
Patent number
US05217964

Reaction notes

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