Boron tribromide → HCID 14860707, compound

HRID 1768685Notes

Reaction equation

HRID 1768685 reaction equation
[C:1]([NH:4][CH:5]([O:16][CH2:17][CH3:18])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:3])[CH3:2].B(Br)(Br)Br.O([C:25]1[CH:30]=CC=[CH:27][CH:26]=1)[Na]>>[C:1]([NH:4][CH:5]([O:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:30][CH:18]=1)[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 25134Boron tribromideHCID 14212862HCID 14212862, compoundHCID 178507098HCID 178507098, compound

Product 1

HCID 14860707HCID 14860707, compound

Procedure

Using 2-acetamido-N-benzyl-2-ethoxyacetamide (3.00 g, 12.0 mmol), BBr3 (1M in CH2Cl2, 15.0 mL, 15.0 mmol), and NaOPh (4.18 g, 30 mmol) gave a brown oily residue which was purified by flash column chromatography on SiO2 gel using first CHCl3 and then 2% MeOH/CHCl3 as the eluents to give the desired product. The compound was recrystallized from chloroform/hexane.

Workup

  1. customgave a brown oily residue which
  2. customwas purified by flash column chromatography on SiO2 gel

Sources & evidence

ORD record
ord-49eeb4d377114c41bd47371bbe8cf454
Source dataset
uspto-grants-1995_01
Patent number
US05378729

Reaction notes

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