Dichloromethane → HCID 178458930, compound

HRID 1650720Notes

Reaction equation

HRID 1650720 reaction equation
[C:1]1([C:7]2[C:8]([OH:32])=[C:9]([C:24]([NH:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[O:25])[C:10]([CH:19]([O:22]C)[CH2:20][CH3:21])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.B(Br)(Br)Br>O>[C:1]1([C:7]2[C:8]([OH:32])=[C:9]([C:24]([NH:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[O:25])[C:10]([CH:19]([OH:22])[CH2:20][CH3:21])=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 178459021HCID 178459021, compound

Product 1

HCID 178458930HCID 178458930, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.65 g of the product of Step F and 86 ml of methylene chloride was cooled to -70° C. to -60° C. and while maintaining this temperature, 116 ml of a solution of boron tribromide were added. After stirring for 24 hours, the temperature was allowed to return to ambient. The solution was poured into 180 ml of iced water and extracted with methylene chloride. The extracts were washed with water, dried and concentrated under reduced pressure. After chromatography under pressure (methylene-chloride - ethyl acetate 8-2), 4 g of the expected product were obtained which after crystallization from ethyl acetate melted at 232° to 234° C.

Workup

  1. additionwere added
  2. extractionextracted with methylene chloride
  3. washThe extracts were washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c9002cad4ac4ca69eb2ff4a05192d5e
Source dataset
uspto-grants-1990_05
Patent number
US04925859

Reaction notes

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