Hydrogen Bromide → HCID 59124005, compound

HRID 1380608Notes

Reaction equation

HRID 1380608 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:11]([CH:13]=[N+]=[N-])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[BrH:23].CCOCC>O1CCCC1.C(OCC)(=O)C>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:11]([CH2:13][Br:23])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 131714612HCID 131714612, compound

Product 1

HCID 59124005HCID 59124005, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Boc-TyrCHN2 (0.40 g, 1.32 mmoles) was dissolved in 20 mL of tetrahydrofuran, and the resulting solution was cooled to about -10°. Anhydrous HBr: ether (2.3M, 0.58 mL, 1.3 mmoles) was added, and after about 5 minutes, solvent was evaporated, leaving a residue. The residue was dissolved in ethyl acetate, and the resulting solution was washed with water and saturated aqueous sodium chloride. The solution was then dried over anhydrous sodium sulfate and ethyl acetate was evaporated, yielding an oil. The oil was applied to a 2 cm column containing 10 g of silica gel, and the column eluted with chloroform. Eluate solvent was evaporated, and the remaining residue was triturated with hexane to yield crystalline Boc-TyrCH2Br (0.22 g, mp 109.5°-111°).

Workup

  1. temperaturethe resulting solution was cooled to about -10°
  2. customsolvent was evaporated
  3. customleaving a residue
  4. washthe resulting solution was washed with water and saturated aqueous sodium chloride
  5. dry with materialThe solution was then dried over anhydrous sodium sulfate and ethyl acetate
  6. customwas evaporated
  7. customyielding an oil
  8. additioncontaining 10 g of silica gel
  9. washthe column eluted with chloroform
  10. customEluate solvent was evaporated
  11. customthe remaining residue was triturated with hexane

Sources & evidence

ORD record
ord-2d44bc91e7aa4505abda8c92c2674025
Source dataset
uspto-grants-1986_04
Patent number
US04582821

Reaction notes

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