Acetic Acid → ((r)-7-Bromo-2-oxo-2,3,4,5-tetrahydro-1h-1-benzazepin-3-yl)-carbamic acid tert-butyl ester

HRID 1364205Notes

Reaction equation

HRID 1364205 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[Br:25]Br>C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[CH2:9][CH2:10][C:11]2[CH:19]=[C:18]([Br:25])[CH:17]=[CH:16][C:12]=2[NH:13][C:14]1=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 10923829(R)-(2-Oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 57779789((r)-7-Bromo-2-oxo-2,3,4,5-tetrahydro-1h-1-benzazepin-3-yl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A round-bottom flask containing ((R)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)-carbamic acid tert-butyl ester (0.338 g, 1.20 mmol) was fitted with a stirbar and septa. Acetic acid (glacial, 5 mL) and bromine (0.37 g, 2.3 mmol) were added, in that order, giving a solution that was stirred at room temperature for 1.5 hours. The reaction was then poured into ethyl acetate (50 mL) and washed with saturated aqueous NaHCO3 solution (2×50 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give an oil that was purified via flash chromatography on silica gel (10% to 50% ethyl acetate/hexanes linear gradient) to give the desired product.

Workup

  1. customwas fitted with a stirbar and septa
  2. customgiving a solution that
  3. washwashed with saturated aqueous NaHCO3 solution (2×50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give an oil that
  8. customwas purified via flash chromatography on silica gel (10% to 50% ethyl acetate/hexanes linear gradient)

Sources & evidence

ORD record
ord-5b7bdc9d0c34428987f3c07d549daa03
Source dataset
uspto-grants-2011_02
Patent number
US07888345B2

Reaction notes

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