Benzyl Bromide → HCID 15859209, compound

HRID 583299Notes

Reaction equation

HRID 583299 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[H-].[Na+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.CCOCC>[CH2:25]([O:16][C:15](=[O:17])[C:14]1[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:13]=1[N:12]([CH2:15][C:14]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:13]=1)[S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 17866403HCID 17866403, compound

Product 1

HCID 15859209HCID 15859209, compoundYield 155%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.82 g (5.66 mmol) of the product of Example 4 in 20 ml DMF, was added NaH (60% suspension in oil, 498 mg, (12.5 mmol). The resulting mixture was stired for 15 minutes and benzyl bromide (4.84 g, 0.028 mol) was then added. The mixture was heated to 80-84° with stirnng for 18 hr under N2. The motion was then cooled to room temperature, diluted with ether, washed with H2O and brine, dried over MgSO4 and concentrated in vacuo. The residue was triturated with EtOAc to afford 2.2 g (77%) of the desired product as a white solid. Electrospray Mass Spec: 502 (M+H).

Workup

  1. temperatureThe mixture was heated to 80-84° with stirnng for 18 hr under N2
  2. washwashed with H2O and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with EtOAc

Sources & evidence

ORD record
ord-005a37398c8743e192f5d92514c755f8
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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