Benzyl Chloride → HCID 485902, compound

HRID 263874Notes

Reaction equation

HRID 263874 reaction equation
[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]2[N:6]([C@@H:10]3[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]3[OH:12])[C:7](=[S:9])[NH:8][C:4]=2[CH:3]=1.[OH-].[NH4+].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(Cl)Cl.CO>O>[CH2:24]([S:9][C:7]1[N:6]([C@@H:10]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]2[OH:12])[C:5]2[CH:19]=[C:20]([Cl:21])[C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 14923Ammonium HydroxideHCID 3000467HCID 3000467, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 485902HCID 485902, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 53 (0.5 g) was dissolved in cold water (10 ml) containing concentrated ammonium hydroxide (2.5 ml). Benzyl chloride (0.5 ml) was added to this solution with stirring and the stirring continued at room temperature for 5 hours. The white solid (0.41 g) which had separated from solution was collected by filtration, washed with cold water. The solid was extracted with ethyl acetate (100 ml) and the ethyl acetate phase was dried over anhydrous Na2SO4 and then evaporated by aspirator to give a syrup. The syrup was subjected to a flash column of silica gel with CH2Cl2 --MeOH (15:1) as eluant. Fractions were collected (25 ml each) and fractions containing the desired compound were combined and evaporated to afford 54 which was crystallized from CH2Cl2 --MeOH (15:1), mp. 149° C., Yield 0.223 g (35.5%).

Workup

  1. customThe white solid (0.41 g) which had separated from solution
  2. filtrationwas collected by filtration
  3. washwashed with cold water
  4. extractionThe solid was extracted with ethyl acetate (100 ml)
  5. dry with materialthe ethyl acetate phase was dried over anhydrous Na2SO4
  6. customevaporated by aspirator
  7. customto give a syrup
  8. customFractions were collected (25 ml each) and fractions
  9. additioncontaining the desired compound
  10. customevaporated

Sources & evidence

ORD record
ord-3e1089b68ba045929c7844630b189218
Source dataset
uspto-grants-1997_07
Patent number
US05646125

Reaction notes

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