Benzyl Chloride → HCID 19906255, compound

HRID 2371668Notes

Reaction equation

HRID 2371668 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[CH:12]([CH3:14])[NH:13][C:8]=2[CH:7]=[C:6]([NH:22][C:23](=[O:27])[O:24][CH2:25][CH3:26])[N:5]=1.[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[NH2:3][C:4]1[C:9]2[N:10]=[C:11]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:19][CH:20]=3)[CH:12]([CH3:14])[NH:13][C:8]=2[CH:7]=[C:6]([NH:22][C:23](=[O:27])[O:24][CH2:25][CH3:26])[N:5]=1

Participants

4

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 459870HCID 459870, compound

Product 1

HCID 19906255HCID 19906255, compound

Procedure

To a stirred suspension of NaH (13.5 mg of 60% oil-dispersion, washed 1× hexane) in deoxygenated (N2) DMSO was added 14 (101 mg, 0.30 mmol). After stirring 0.2 hour, the nearly-clear amber solution was treated with benzyl chloride (36 mg, 0.29 mmol), stirred 18 hours under N2, and evaporated to dryness. The residue was triturated with de-oxygenated (N2) H2O (10 mL) to give a solid, which was purified by flash chromatography (45 g, CHCl3 --MeOH, 99:1) followed by recrystallization from EtOAc-hexane to afford 17 as a pale yellow solid: yield, 44 mg.

Workup

  1. customin deoxygenated (N2) DMSO
  2. stirringstirred 18 hours under N2
  3. customevaporated to dryness
  4. customThe residue was triturated with de-oxygenated (N2) H2O (10 mL)
  5. customto give a solid, which
  6. customwas purified by flash chromatography (45 g, CHCl3 --MeOH, 99:1)
  7. customfollowed by recrystallization from EtOAc-hexane

Sources & evidence

ORD record
ord-1c2e02b26da74a309836294953d98565
Source dataset
uspto-grants-1992_03
Patent number
US05095017

Reaction notes

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