Boron tribromide → HCID 66783355, compound

HRID 1096200Notes

Reaction equation

HRID 1096200 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@@H:4]([N:15]1[C:21](=[O:22])[CH2:20][CH2:19][N:18]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[CH2:17][CH2:16]1)[CH2:5][CH2:6][O:7]CC1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl.B(Br)(Br)Br>[CH3:1][O:2][C:3](=[O:31])[C@@H:4]([N:15]1[C:21](=[O:22])[CH2:20][CH2:19][N:18]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[CH2:17][CH2:16]1)[CH2:5][CH2:6][OH:7]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 66783219HCID 66783219, compound

Product 1

HCID 66783355HCID 66783355, compoundYield 119.9%

Reagents, catalysts & solvents 2

HCID 25134Boron tribromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.05 g (4.40 mmol) of (S)-4-benzyloxy-2-[4-(3,4-dichloro-phenyl)-7-oxo-[1,4]diazepan-1-yl]-butyric acid methyl ester (evaporated with toluene) in 20 ml CH2Cl2 was cooled (−20° C.) and treated with 4.62 ml (4.62 mmol, 1M in CH2Cl2) of boron tribromide. The solution was warmed in 1 h to 0° C. and kept for 1.5 h at this temperature, additional 0.22 ml (0.22 mmol, 1M in CH2Cl2) of boron tribromide was added and stirring was continued for 30 min. The mixture was extracted with cold sat. aq. NaHCO3 solution and EtOAc (3×). The organic phases were washed with sat. aq. NaHCO3 solution, aq. 10% NaCl solution, dried over Na2SO4 evaporated to give 1.98 g (76%) of the title compound as light yellow foam. MS: 375.2 (MH+, 2Cl).

Workup

  1. temperatureThe solution was warmed in 1 h to 0° C.
  2. additionwas added
  3. extractionThe mixture was extracted with cold sat. aq. NaHCO3 solution and EtOAc (3×)
  4. washThe organic phases were washed with sat. aq. NaHCO3 solution, aq. 10% NaCl solution
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-792567e4e568420fb996b6e4d08c188b
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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